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C1=CC(=C(C=C1CC#N)F)ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-(4-chloro-3-fluorophenyl)acetonitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 251570-03-3 |
| Database ID | 3804414 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-(4-chloro-3-fluorophenyl)acetonitrile (CAS 251570-03-3) 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 3804414
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-4378b3039f87425c9f3c22992d91d41aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0d8c6d81cd5a4550b10e1120ef06ed99Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-986139d3ce264aa7a9b914e0bae24e49Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4378b3039f87425c9f3c22992d91d41aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of the product of example 26 (7.8 g, 0.046 mol), water (7.5 ml), concentrated sulfuric acid (7.5 ml) and acetic acid (7.5 ml) was heated at reflux for 2 hours. After being cooled to room temperature, the mixture was poured into ice-water. The resulting solids were collected by filtration and washed by diethyl ether to give the titled product (6.8 g, 79%) was heated at reflux for 2 hours The resulting solids were collected by filtration washed by diethyl ether
Source ID: ord-4c4376493af24324a843f4143b068cd5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of the product of example 26 (7.8 g, 0.046 mol), water (7.5 ml), concentrated sulfuric acid (7.5 ml) and acetic acid (7.5 ml) was heated at reflux for 2 hours. After being cooled to room temperature, the mixture was poured into ice-water. The resulting solids were collected by filtration and washed by diethyl ether to give the titled product (6.8 g, 79%) was heated at reflux for 2 hours The resulting solids were collected by filtration washed by diethyl ether
Source ID: ord-4c4376493af24324a843f4143b068cd5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 60% NaH (1.07 g, 26.7 mmol) was added in 2 portions to a 0° C. solution of 2-(4-chloro-3-fluorophenyl)acetonitrile (1.81 g, 10.7 mmol) and 15-crown-5 (0.235 g, 1.07 mmol) in DMF (45 mL). The reaction mixture was warmed to room temperature and stirred for 35 minutes. The reaction mixture was then cooled to 0° C. NaI (1.60 g, 10.7 mmol) was added, and then a solution of freshly prepared tert-butyl bis(2-chloroethyl)carbamate (2.58 g, 10.7 mmol) in DMF (10 mL) was added by syringe. The reaction mixture was warmed to room temperature and stirred overnight (19 hours). The reaction mixture was poured into ice saturated NH4Cl, and the mixture was extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was flashed on silica (Biotage 40L, 9:1 hex:EtOAc until product eluted, then 6:1 hex:EtOAc to elute product) to give tert-butyl 4-(4-chloro-3-fluorophenyl)-4-cyanopiperidine-1-carboxylate (1.96 g, 54.2% yield) as a yellow oil. LC/MS (APCI+) m/z 239 [M-Boc+H]+. The reaction mixture was then cooled to 0° C The reaction mixture was warmed to room temperature stirred overnight (19 hours) The reaction mixture was poured into ice saturated NH4Cl the mixture was extracted with EtOAc The combined extracts were dried (Na2SO4) filtered concentrated EtOAc until product eluted 6:1 hex:EtOAc to elute product)
Source ID: ord-a26c88b847fe47dfad5781c6a8f96a5eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: KCN (1.25 g, 19.2 mmol) was added to a solution of 4-(bromomethyl)-1-chloro-2-fluorobenzene (3.90 g, 17.5 mmol) in DMSO (60 mL). Several milliliters of H2O were added to help dissolve the KCN. After 1 hour, the reaction mixture was diluted with H2O and extracted with EtOAc. The extracts were dried (Na2SO4), filtered, and concentrated. The crude product was flashed on silica (Biotage 40M, 9:1 to 4:1 hex:EtOAc) to give 2-(4-chloro-3-fluorophenyl)acetonitrile (1.81 g, 61.2% yield) as a yellow crystalline solid. extracted with EtOAc The extracts were dried (Na2SO4) filtered concentrated
Source ID: ord-a278ca2cf4b44fb3946069a8b916d643Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 60% NaH (1.07 g, 26.7 mmol) was added in 2 portions to a 0° C. solution of 2-(4-chloro-3-fluorophenyl)acetonitrile (1.81 g, 10.7 mmol) and 15-crown-5 (0.235 g, 1.07 mmol) in DMF (45 mL). The reaction mixture was warmed to room temperature and stirred for 35 minutes. The reaction mixture was then cooled to 0° C. NaI (1.60 g, 10.7 mmol) was added, and then a solution of freshly prepared tert-butyl bis(2-chloroethyl)carbamate (2.58 g, 10.7 mmol) in DMF (10 mL) was added by syringe. The reaction mixture was warmed to room temperature and stirred overnight (19 hours). The reaction mixture was poured into ice saturated NH4Cl, and the mixture was extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was flashed on silica (Biotage 40 L, 9:1 hex:EtOAc until product eluted, then 6:1 hex:EtOAc to elute product) to give tert-butyl 4-(4-chloro-3-fluorophenyl)-4-cyanopiperidine-1-carboxylate (1.96 g, 54.2% yield) as a yellow oil. LC/MS (APCI+) m/z 239 [M−Boc+H]+. The reaction mixture was then cooled to 0° C The reaction mixture was warmed to room temperature stirred overnight (19 hours) The reaction mixture was poured into ice saturated NH4Cl the mixture was extracted with EtOAc The combined extracts were dried (Na2SO4) filtered concentrated EtOAc until product eluted 6:1 hex:EtOAc to elute product)
Source ID: ord-7257fda6078c4e74b71a88f9d4ff9285Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 60% NaH (1.07 g, 26.7 mmol) was added in 2 portions to a 0° C. solution of 2-(4-chloro-3-fluorophenyl)acetonitrile (1.81 g, 10.7 mmol) and 15-crown-5 (0.235 g, 1.07 mmol) in DMF (45 mL). The reaction mixture was warmed to room temperature and stirred for 35 minutes. The reaction mixture was then cooled to 0° C. NaI (1.60 g, 10.7 mmol) was added, and then a solution of freshly prepared tert-butyl bis(2-chloroethyl)carbamate (2.58 g, 10.7 mmol) in DMF (10 mL) was added by syringe. The reaction mixture was warmed to room temperature and stirred overnight (19 hours). The reaction mixture was poured into ice saturated NH4Cl, and the mixture was extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was flashed on silica (Biotage 40 L, 9:1 hex:EtOAc until product eluted, then 6:1 hex:EtOAc to elute product) to give tert-butyl 4-(4-chloro-3-fluorophenyl)-4-cyanopiperidine-1-carboxylate (1.96 g, 54.2% yield) as a yellow oil. LC/MS (APCI+) m/z 239 [M−Boc+H]+. The reaction mixture was then cooled to 0° C The reaction mixture was warmed to room temperature stirred overnight (19 hours) The reaction mixture was poured into ice saturated NH4Cl the mixture was extracted with EtOAc The combined extracts were dried (Na2SO4) filtered concentrated EtOAc until product eluted 6:1 hex:EtOAc to elute product)
Source ID: ord-7257fda6078c4e74b71a88f9d4ff9285Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: KCN (1.25 g, 19.2 mmol) was added to a solution of 4-(bromomethyl)-1-chloro-2-fluorobenzene (3.90 g, 17.5 mmol) in DMSO (60 mL). Several milliliters of H2O were added to help dissolve the KCN. After 1 hour, the reaction mixture was diluted with H2O and extracted with EtOAc. The extracts were dried (Na2SO4), filtered, and concentrated. The crude product was flashed on silica (Biotage 40M, 9:1 to 4:1 hex:EtOAc) to give 2-(4-chloro-3-fluorophenyl)acetonitrile (1.81 g, 61.2% yield) as a yellow crystalline solid. extracted with EtOAc The extracts were dried (Na2SO4) filtered concentrated
Source ID: ord-d5531e5b49e646718f382b4858cdee01Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: KCN (1.25 g, 19.2 mmol) was added to a solution of 4-(bromomethyl)-1-chloro-2-fluorobenzene (3.90 g, 17.5 mmol) in DMSO (60 mL). Several milliliters of H2O were added to help dissolve the KCN. After 1 hour, the reaction mixture was diluted with H2O and extracted with EtOAc. The extracts were dried (Na2SO4), filtered, and concentrated. The crude product was flashed on silica (Biotage 40M, 9:1 to 4:1 hex:EtOAc) to give 2-(4-chloro-3-fluorophenyl)acetonitrile (1.81 g, 61.2% yield) as a yellow crystalline solid. extracted with EtOAc The extracts were dried (Na2SO4) filtered concentrated
Source ID: ord-d5531e5b49e646718f382b4858cdee01PubChem References
These sources are listed in the compound's public database record.
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