3,5-Difluorophenylacetonitrile → 2-(3,5-Difluorophenyl)ethan-1-amine

HRID 14858Notes

Reaction equation

HRID 14858 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[C:6]([F:8])[CH:7]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH2:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 1

HCID 5185653,5-Difluorophenylacetonitrile

Product 1

HCID 36736652-(3,5-Difluorophenyl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,5 difluorophenylacetonitrile (5 g) was dissolved in THF (100 mL) and a solution of BH3 in THF (200 mL of 1 M) was added dropwise. The mixture was refluxed overnight, cooled in an ice bath, and the reaction quenched with methanol (20 mL). The solvent was removed by rotary evaporation and the residue partitioned between ethyl acetate and water. The organic layer was washed with sat NaCl and the solvent again removed to give product, which was used in the next step without purification.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperaturecooled in an ice bath
  3. customthe reaction quenched with methanol (20 mL)
  4. customThe solvent was removed by rotary evaporation
  5. customthe residue partitioned between ethyl acetate and water
  6. washThe organic layer was washed with sat NaCl
  7. customthe solvent again removed
  8. customto give product, which
  9. customwas used in the next step without purification

Sources & evidence

ORD record
ord-8a2a855870d44d539cb30855779f6c30
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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