Methanol → 2-(3-Chloro-2-fluorophenyl)ethanamine

HRID 2277578Notes

Reaction equation

HRID 2277578 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.B.CO>C1COCC1>[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 27737242-(3-Chloro-2-fluorophenyl)acetonitrile

Product 1

HCID 534035832-(3-Chloro-2-fluorophenyl)ethanamineYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-chloro-2-fluoro-phenyl)-acetonitrile (1.48 g, 8.8 mmol) in anhydrous THF (20 mL) was added a solution of borane (20 mL, 1M in THF) dropwise. The resulting reaction mixture was heated at reflux temperature for 2 hours. After cooling to room temperature, MeOH was added and the mixture was stirred at room temperature for additional 30 min. After removal of volatiles under reduced pressure, desired title product (1.30 g, 90%) was obtained as oil. MS: 174.0 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux temperature for 2 hours
  4. customAfter removal of volatiles under reduced pressure

Sources & evidence

ORD record
ord-c55e2cb4209f4c8fbe6ae01e86124df8
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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