No renderable structure data available
FC1C=C2C(CC(N2)=O)=CC=1FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 5,6-Difluoro-2-oxoindole |
|---|---|
| IUPAC Name | — |
| CAS Number | 71294-07-0 |
| Database ID | 12585282 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
5,6-Difluoro-2-oxoindole (CAS 71294-07-0) 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 12585282
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-fa600020e9414083b6cfc336c28a537eConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5, 6-difluorooxindole (450 mg, 2.66 mmol) in THF (20 mL) at 0° C., was added 1 M LiHMDS in THF (5.3 mL, 5.3 mmol). The reaction mixture was stirred at 0° C. for 10 minutes. 4-bromo-5, 5-dimethyl-5H-furan-2-one (340 mg, 1.78 mmol) was then added. The reaction mixture was stirred at 0° C. for 30 min., and then at room temperature for an additional 30 min and quenched with 2.5M aqueous H2SO4 (3 mL). The resulting mixture was stirred at room temperature for 16 hours and poured into water (100 mL). The precipitates were filtered, washed with water and dried in vacuo to yield (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-5,6-difluoro-1,3-dihydro-2H-indol-2-one as yellow solid. Yield: 547 mg, 90%. The reaction mixture was stirred at 0° C. for 30 min. at room temperature for an additional 30 min quenched with 2.5M aqueous H2SO4 (3 mL) The resulting mixture was stirred at room temperature for 16 hours poured into water (100 mL) The precipitates were filtered washed with water dried in vacuo
Source ID: ord-46e2cd66b1f544aa95854604b132a2b4Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5,6-difluorooxindole (450 mg, 2.66 mmol) in THF (20 mL) at 0° C., was added 1M LiHMDS in THF (5.3 mL, 5.3 mmol). The reaction mixture was stirred at 0° C. for 10 minutes. 4-bromo-5,5-dimethyl-5H-furan-2-one (340 mg, 1.78 mmol) was then added. The reaction mixture was stirred at 0° C. for 30 min., and then at room temperature for an additional 30 min and quenched with 2.5M aqueous H2SO4 (3 mL). The resulting mixture was stirred at room temperature for 16 hours and poured into water (100 mL). The precipitates were filtered, washed with water and dried in vacuo to yield (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-5,6-difluoro-1,3-dihydro-2H-indol-2-one as yellow solid. Yield: 547 mg, 90%. The reaction mixture was stirred at 0° C. for 30 min. at room temperature for an additional 30 min quenched with 2.5M aqueous H2SO4 (3 mL) The resulting mixture was stirred at room temperature for 16 hours poured into water (100 mL) The precipitates were filtered washed with water dried in vacuo
Source ID: ord-89f1320c7f554238845fc62f17f194f5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-(3,4-difluorophenyl)chloroacetamide (14 mmol) and aluminum chloride (54 mmol) was stirred and heated to 200-210 deg C. in a silicon oil bath for 4.5 h. On cooling, 40 mL of ice cold hydrochloric acid was added to the reaction mixture. The solid residue was removed by vacuum filtration and purified by column chromatography with hexane-ethyl acetate (1:1) as eluting solvent. The yield for this step was 40.7%. 1HNMR (300 MHz, in DMSO-d6) δ 10.46 (s, 1H, NH), 7.33 (t, J=8.7 Hz, 1H, Ar—H), 6.82 (q, J=6.9 Hz, 1H, Ar—H), 3.47 (s, 2H, ArCH2CO). heated to 200-210 deg C On cooling The solid residue was removed by vacuum filtration purified by column chromatography with hexane-ethyl acetate (1:1) as eluting solvent The yield for this step
Source ID: ord-87b72d0d0a474ec1a5c5d5a7607c2ea2Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-fa600020e9414083b6cfc336c28a537eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-fa600020e9414083b6cfc336c28a537eConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5,6-difluorooxindole (450 mg, 2.66 mmol) in THF (20 mL) at 0° C., was added 1 M LiHMDS in THF (5.3 mL, 5.3 mmol). The reaction mixture was stirred at 0° C. for 10 minutes. 4-bromo-5,5-dimethyl-5H-furan-2-one (340 mg, 1.78 mmol) was then added. The reaction mixture was stirred at 0° C. for 30 min., and then at room temperature for an additional 30 min and quenched with 2.5M aqueous H2SO4 (3 mL). The resulting mixture was stirred at room temperature for 16 hours and poured into water (100 mL). The precipitates were filtered, washed with water and dried in vacuo to yield (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-5,6-difluoro-1,3-dihydro-2H-indol-2-one as yellow solid. Yield: 547 mg, 90%. The reaction mixture was stirred at 0° C. for 30 min. at room temperature for an additional 30 min quenched with 2.5M aqueous H2SO4 (3 mL) The resulting mixture was stirred at room temperature for 16 hours poured into water (100 mL) The precipitates were filtered washed with water dried in vacuo
Source ID: ord-82df3492b717408eb709fc13936623a4Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5, 6-difluorooxindole (450 mg, 2.66 mmol) in THF (20 mL) at 0° C., was added 1 M LiHMDS in THF (5.3 mL, 5.3 mmol). The reaction mixture was stirred at 0° C. for 10 minutes. 4-bromo-5, 5-dimethyl-5H-furan-2-one (340 mg, 1.78 mmol) was then added. The reaction mixture was stirred at 0° C. for 30 min., and then at room temperature for an additional 30 min and quenched with 2.5M aqueous H2SO4 (3 mL). The resulting mixture was stirred at room temperature for 16 hours and poured into water (100 mL). The precipitates were filtered, washed with water and dried in vacuo to yield (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-5,6-difluoro-1,3-dihydro-2H-indol-2-one as yellow solid. Yield: 547 mg, 90%. The reaction mixture was stirred at 0° C. for 30 min. at room temperature for an additional 30 min quenched with 2.5M aqueous H2SO4 (3 mL) The resulting mixture was stirred at room temperature for 16 hours poured into water (100 mL) The precipitates were filtered washed with water dried in vacuo
Source ID: ord-46e2cd66b1f544aa95854604b132a2b4Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5, 6-difluorooxindole (450 mg, 2.66 mmol) in THF (20 mL) at 0° C., was added 1 M LiHMDS in THF (5.3 mL, 5.3 mmol). The reaction mixture was stirred at 0° C. for 10 minutes. 4-bromo-5, 5-dimethyl-5H-furan-2-one (340 mg, 1.78 mmol) was then added. The reaction mixture was stirred at 0° C. for 30 min., and then at room temperature for an additional 30 min and quenched with 2.5M aqueous H2SO4 (3 mL). The resulting mixture was stirred at room temperature for 16 hours and poured into water (100 mL). The precipitates were filtered, washed with water and dried in vacuo to yield (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-5,6-difluoro-1,3-dihydro-2H-indol-2-one as yellow solid. Yield: 547 mg, 90%. The reaction mixture was stirred at 0° C. for 30 min. at room temperature for an additional 30 min quenched with 2.5M aqueous H2SO4 (3 mL) The resulting mixture was stirred at room temperature for 16 hours poured into water (100 mL) The precipitates were filtered washed with water dried in vacuo
Source ID: ord-46e2cd66b1f544aa95854604b132a2b4Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5,6-difluorooxindole (450 mg, 2.66 mmol) in THF (20 mL) at 0° C., was added 1M LiHMDS in THF (5.3 mL, 5.3 mmol). The reaction mixture was stirred at 0° C. for 10 minutes. 4-bromo-5,5-dimethyl-5H-furan-2-one (340 mg, 1.78 mmol) was then added. The reaction mixture was stirred at 0° C. for 30 min., and then at room temperature for an additional 30 min and quenched with 2.5M aqueous H2SO4 (3 mL). The resulting mixture was stirred at room temperature for 16 hours and poured into water (100 mL). The precipitates were filtered, washed with water and dried in vacuo to yield (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-5,6-difluoro-1,3-dihydro-2H-indol-2-one as yellow solid. Yield: 547 mg, 90%. The reaction mixture was stirred at 0° C. for 30 min. at room temperature for an additional 30 min quenched with 2.5M aqueous H2SO4 (3 mL) The resulting mixture was stirred at room temperature for 16 hours poured into water (100 mL) The precipitates were filtered washed with water dried in vacuo
Source ID: ord-89f1320c7f554238845fc62f17f194f5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-(3,4-difluorophenyl)chloroacetamide (14 mmol) and aluminum chloride (54 mmol) was stirred and heated to 200-210 deg C. in a silicon oil bath for 4.5 h. On cooling, 40 mL of ice cold hydrochloric acid was added to the reaction mixture. The solid residue was removed by vacuum filtration and purified by column chromatography with hexane-ethyl acetate (1:1) as eluting solvent. The yield for this step was 40.7%. 1HNMR (300 MHz, in DMSO-d6) δ 10.46 (s, 1H, NH), 7.33 (t, J=8.7 Hz, 1H, Ar—H), 6.82 (q, J=6.9 Hz, 1H, Ar—H), 3.47 (s, 2H, ArCH2CO). heated to 200-210 deg C On cooling The solid residue was removed by vacuum filtration purified by column chromatography with hexane-ethyl acetate (1:1) as eluting solvent The yield for this step
Source ID: ord-87b72d0d0a474ec1a5c5d5a7607c2ea2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of N-(3,4-difluorophenyl)chloroacetamide (14 mmol) and aluminum chloride (54 mmol) was stirred and heated to 200-210 deg C. in a silicon oil bath for 4.5 h. On cooling, 40 mL of ice cold hydrochloric acid was added to the reaction mixture. The solid residue was removed by vacuum filtration and purified by column chromatography with hexane-ethyl acetate (1:1) as eluting solvent. The yield for this step was 40.7%. 1HNMR (300 MHz, in DMSO-d6) δ 10.46 (s, 1H, NH), 7.33 (t, J=8.7 Hz, 1H, Ar—H), 6.82 (q, J=6.9 Hz, 1H, Ar—H), 3.47 (s, 2H, ArCH2CO). heated to 200-210 deg C On cooling The solid residue was removed by vacuum filtration purified by column chromatography with hexane-ethyl acetate (1:1) as eluting solvent The yield for this step
Source ID: ord-87b72d0d0a474ec1a5c5d5a7607c2ea2PubChem References
These sources are listed in the compound's public database record.
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