Methanol → (2-Fluoro-6-(trifluoromethyl)phenyl)methanamine

HRID 1827912Notes

Reaction equation

HRID 1827912 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:3]=1[C:4]#[N:5].CO>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[C:3]=1[CH2:4][NH2:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 1456132-Fluoro-6-(trifluoromethyl)benzonitrile

Product 1

HCID 2774790(2-Fluoro-6-(trifluoromethyl)phenyl)methanamineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 2-fluoro-6-(trifluoromethyl)benzonitrile (45 g, 0.238 mmol) in 60 mL of THF was added 1 M BH3:THF slowly at 60° C. and the resulting solution was refluxed overnight. The reaction mixture was cooled to ambient temperature. Methanol (420 mL) was added slowly and stirred well. The solvents were then evaporated and the residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4. Evaporation gave 1a as a yellow oil (46 g, 0.238 mmol). MS (CI) m/z 194.0 (MH+).

Workup

  1. customThe solvents were then evaporated
  2. customthe residue was partitioned between EtOAc and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customEvaporation

Sources & evidence

ORD record
ord-9137121197c34a159bc3210bfce7fee4
Source dataset
uspto-grants-2006_06
Patent number
US07056927B2

Reaction notes

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