No renderable structure data available
FC1C=C(C=C2CCCC(C2=1)=O)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 6,8-DIFLUORO-1,2,3,4-TETRAHYDRONAPHTHALEN-1-ONE |
|---|---|
| IUPAC Name | — |
| CAS Number | 895534-38-0 |
| Database ID | 55274581 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
6,8-DIFLUORO-1,2,3,4-TETRAHYDRONAPHTHALEN-1-ONE (CAS 895534-38-0) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 55274581
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-299f6f7a0d824188922a23c5ecdcac27Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7e1942e984dc4f44bda753b6c536b5a1Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 6,8-difluoro-3,4-dihydro-2H-naphthalen-1-one (1.0 gram, 5.5 moles) and potassium thiophenolate (0.81 gram, 5.5 mmole) in 4 mL DMSO was heated at 50° C. for 0.5 hour. The mixture was diluted with 30 mL 0.1N hydrochloric acid and then it was extracted with 50 mL diethyl ether. The organic phase was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. 8-Fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one was obtained by recrystallization of the residue from ethyl acetate/hexane, 0.871 gram (58%), m.p. 112-113° C., M+H=273. it was extracted with 50 mL diethyl ether The organic phase was washed with water dried (magnesium sulfate) concentrated under reduced pressure
Source ID: ord-42171410f7da43f7aac848a784776060Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This step follows the general procedure reported by Eaton et al., Organic Chemistry 38(23): 4071-4073 (1973). Eaton's reagent, prepared from 32 g phosphorus pentoxide and 192 mL methanesulfonic acid, was heated at 65° C. A solution of 4-(3,5-difluoro-phenyl)-butyric acid (12.85 grams, 64.19 mmoles, prepared as described by Repke et al., U.S. Pat. No. 5,538,988) in 30 mL methanesulfonic acid was added and the reaction mixture was heated at 65° C. for 35 minutes. The mixture was poured onto 1 L cracked ice and the product was extracted twice with 500 mL of a mixture of 2 parts diethyl ether to 1 part ethyl acetate. The organic phase was washed with saturated sodium bicarbonate, water, saturated sodium chloride and then it was dried (magnesium sulfate). The solution was concentrated under reduced pressure. 6,8-Difluoro-3,4-dihydro-2H-naphthalen-1-one was isolated by recrystallization from hexane, 9.55 grams (82%), m.p. 57-58° C. the reaction mixture was heated at 65° C. for 35 minutes The mixture was poured onto 1 L the product was extracted twice with 500 mL of a mixture of 2 parts diethyl ether to 1 part ethyl acetate The organic phase was washed with saturated sodium bicarbonate, water, saturated sodium chloride it was dried (magnesium sulfate) The solution was concentrated under reduced pressure
Source ID: ord-da2a9c00fcd9412c9cb857622fa055bbConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 6,8-difluoro-3,4-dihydro-2H-naphthalen-1-one (1.0 gram, 5.5 moles) and potassium thiophenolate (0.81 gram, 5.5 mmole) in 4 mL DMSO was heated at 50° C. for 0.5 hour. The mixture was diluted with 30 mL 0.1N hydrochloric acid and then it was extracted with 50 mL diethyl ether. The organic phase was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. 8-Fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one was obtained by recrystallization of the residue from ethyl acetate/hexane, 0.871 gram (58%), m.p. 112-113° C., M+H=273. it was extracted with 50 mL diethyl ether The organic phase was washed with water dried (magnesium sulfate) concentrated under reduced pressure
Source ID: ord-b85f6381ee8a4ba98a01120c2a0c922dConditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This step follows the general procedure reported by Eaton et al., Organic Chemistry 38(23): 4071-4073 (1973). Eaton's reagent, prepared from 32 g phosphorus pentoxide and 192 mL methanesulfonic acid, was heated at 65° C. A solution of 4-(3,5-difluoro-phenyl)-butyric acid (12.85 grams, 64.19 mmoles, prepared as described by Repke et al., U.S. Pat. No. 5,538,988) in 30 mL methanesulfonic acid was added and the reaction mixture was heated at 65° C. for 35 minutes. The mixture was poured onto 1 L cracked ice and the product was extracted twice with 500 mL of a mixture of 2 parts diethyl ether to 1 part ethyl acetate. The organic phase was washed with saturated sodium bicarbonate, water, saturated sodium chloride and then it was dried (magnesium sulfate). The solution was concentrated under reduced pressure. 6,8-Difluoro-3,4-dihydro-2H-naphthalen-1-one was isolated by recrystallization from hexane, 9.55 grams (82%), m.p. 57-58° C. the reaction mixture was heated at 65° C. for 35 minutes The mixture was poured onto 1 L the product was extracted twice with 500 mL of a mixture of 2 parts diethyl ether to 1 part ethyl acetate The organic phase was washed with saturated sodium bicarbonate, water, saturated sodium chloride it was dried (magnesium sulfate) The solution was concentrated under reduced pressure
Source ID: ord-dbeeade380bc45c1af472f1789b5a208Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 6,8-difluoro-3,4-dihydro-2H-naphthalen-1-one (1.0 gram, 5.5 moles) and potassium thiophenolate (0.81 gram, 5.5 mmole) in 4 mL DMSO was heated at 50° C. for 0.5 hour. The mixture was diluted with 30 mL 0.1N hydrochloric acid and then it was extracted with 50 mL diethyl ether. The organic phase was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. 8-Fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one was obtained by recrystallization of the residue from ethyl acetate/hexane, 0.871 gram (58%), m.p. 112-113° C., M+H=273. it was extracted with 50 mL diethyl ether The organic phase was washed with water dried (magnesium sulfate) concentrated under reduced pressure
Source ID: ord-26d8df215406484eb46ccf2733addd01Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This step follows the general procedure reported by Eaton et al., Organic Chemistry 38 (23): 4071-4073 (1973). Eaton's reagent, prepared from 32 g phosphorus pentoxide and 192 mL methanesulfonic acid, was heated at 65° C. A solution of 4-(3,5-difluoro-phenyl)-butyric acid (12.85 grams, 64.19 mmoles, prepared as described by Repke et al., U.S. Pat. No. 5,538,988) in 30 mL methanesulfonic acid was added and the reaction mixture was heated at 65° C. for 35 minutes. The mixture was poured onto 1 L cracked ice and the product was extracted twice with 500 mL of a mixture of 2 parts diethyl ether to 1 part ethyl acetate. The organic phase was washed with saturated sodium bicarbonate, water, saturated sodium chloride and then it was dried (magnesium sulfate). The solution was concentrated under reduced pressure. 6,8-Difluoro-3,4-dihydro-2H-naphthalen-1-one was isolated by recrystallization from hexane, 9.55 grams (82%), m.p. 57-58° C. the reaction mixture was heated at 65° C. for 35 minutes The mixture was poured onto 1 L the product was extracted twice with 500 mL of a mixture of 2 parts diethyl ether to 1 part ethyl acetate The organic phase was washed with saturated sodium bicarbonate, water, saturated sodium chloride it was dried (magnesium sulfate) The solution was concentrated under reduced pressure
Source ID: ord-6ca06523b87348188e795fe659fbe018Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This step follows the general procedure reported by Eaton et al., Organic Chemistry 38 (23): 4071-4073 (1973). Eaton's reagent, prepared from 32 g phosphorus pentoxide and 192 mL methanesulfonic acid, was heated at 65° C. A solution of 4-(3,5-difluoro-phenyl)-butyric acid (12.85 grams, 64.19 mmoles, prepared as described by Repke et al., U.S. Pat. No. 5,538,988) in 30 mL methanesulfonic acid was added and the reaction mixture was heated at 65° C. for 35 minutes. The mixture was poured onto 1 L cracked ice and the product was extracted twice with 500 mL of a mixture of 2 parts diethyl ether to 1 part ethyl acetate. The organic phase was washed with saturated sodium bicarbonate, water, saturated sodium chloride and then it was dried (magnesium sulfate). The solution was concentrated under reduced pressure. 6,8-Difluoro-3,4-dihydro-2H-naphthalen-1-one was isolated by recrystallization from hexane, 9.55 grams (82%), m.p. 57-58° C. the reaction mixture was heated at 65° C. for 35 minutes The mixture was poured onto 1 L the product was extracted twice with 500 mL of a mixture of 2 parts diethyl ether to 1 part ethyl acetate The organic phase was washed with saturated sodium bicarbonate, water, saturated sodium chloride it was dried (magnesium sulfate) The solution was concentrated under reduced pressure
Source ID: ord-6ca06523b87348188e795fe659fbe018Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 6,8-difluoro-3,4-dihydro-2H-naphthalen-1-one (1.0 gram, 5.5 moles) and potassium thiophenolate (0.81 gram, 5.5 mmole) in 4 mL DMSO was heated at 50° C. for 0.5 hour. The mixture was diluted with 30 mL 0.1N hydrochloric acid and then it was extracted with 50 mL diethyl ether. The organic phase was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. 8-Fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one was obtained by recrystallization of the residue from ethyl acetate/hexane, 0.871 gram (58%), m.p. 112-113° C., M+H=273. it was extracted with 50 mL diethyl ether The organic phase was washed with water dried (magnesium sulfate) concentrated under reduced pressure
Source ID: ord-3f627217d948420f9759db34425b15caConditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This step follows the general procedure reported by Eaton et al., Organic Chemistry 38(23): 4071-4073 (1973). Eaton's reagent, prepared from 32 g phosphorus pentoxide and 192 mL methanesulfonic acid, was heated at 65° C. A solution of 4-(3,5-difluoro-phenyl)-butyric acid (12.85 grams, 64.19 mmoles, prepared as described by Repke et al., U.S. Pat. No. 5,538,988) in 30 mL methanesulfonic acid was added and the reaction mixture was heated at 65° C. for 35 minutes. The mixture was poured onto 1 L cracked ice and the product was extracted twice with 500 mL of a mixture of 2 parts diethyl ether to 1 part ethyl acetate. The organic phase was washed with saturated sodium bicarbonate, water, saturated sodium chloride and then it was dried (magnesium sulfate). The solution was concentrated under reduced pressure. 6,8-Difluoro-3,4-dihydro-2H-naphthalen-1-one was isolated by recrystallization from hexane, 9.55 grams (82%), m.p. 57-58° C. the reaction mixture was heated at 65° C. for 35 minutes The mixture was poured onto 1 L the product was extracted twice with 500 mL of a mixture of 2 parts diethyl ether to 1 part ethyl acetate The organic phase was washed with saturated sodium bicarbonate, water, saturated sodium chloride it was dried (magnesium sulfate) The solution was concentrated under reduced pressure
Source ID: ord-3c7c1f961d554168a85ae646d71fb3f4Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 6,8-difluoro-3,4-dihydro-2H-naphthalen-1-one (1.0 gram, 5.5 moles) and potassium thiophenolate (0.81 gram, 5.5 mmole) in 4 mL DMSO was heated at 50° C. for 0.5 hour. The mixture was diluted with 30 mL 0.1N hydrochloric acid and then it was extracted with 50 mL diethyl ether. The organic phase was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. 8-Fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one was obtained by recrystallization of the residue from ethyl acetate/hexane, 0.871 gram (58%), m.p. 112-113° C., M+H=273. it was extracted with 50 mL diethyl ether The organic phase was washed with water dried (magnesium sulfate) concentrated under reduced pressure
Source ID: ord-42171410f7da43f7aac848a784776060PubChem References
These sources are listed in the compound's public database record.
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