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

HRID 2386459Notes

Reaction equation

HRID 2386459 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 8028TetrahydrofuranSolvent

Procedure

3,5 difluorophenylacetonitrile (5 g) was dissolved in TI-IF (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-eacd52eb4c334d768360f43232d0cb3e
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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