N-(1-(2-Bromo-4-fluorophenyl)ethyl)-2,2-difluoroacetamide → N-(1-(2-Bromo-4-fluorophenyl)ethyl)-2,2-difluoroethanamine

HRID 558143Notes

Reaction equation

HRID 558143 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:11][C:12](=O)[CH:13]([F:15])[F:14])[CH3:10]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:11][CH2:12][CH:13]([F:15])[F:14])[CH3:10]

Participants

3

Reactant 1

HCID 57445093N-(1-(2-Bromo-4-fluorophenyl)ethyl)-2,2-difluoroacetamide

Product 1

HCID 86640661N-(1-(2-Bromo-4-fluorophenyl)ethyl)-2,2-difluoroethanamineYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add borane-THF complex (10.69 mL, 10.7 mmol) to a solution of N-(1-(2-bromo-4-fluorophenyl)ethyl)-2,2-difluoroacetamide (1.06 g, 3.56 mmol) in THF (3 mL). Reflux the mixture for 17 h. Quench with hydrochloric acid (5 N, 8 mL). Stir the solution for 1 h. Add saturated NaHCO3. Dilute the mixture with DCM, wash with water and aqueous saturated sodium chloride. Separate the organic layer and dry over sodium sulfate. Filter and concentrate in vacuo to give the title compound (0.94 g, 93%). MS (ES) m/z 282 [M+1]+.

Workup

  1. temperatureReflux the mixture for 17 h
  2. customQuench with hydrochloric acid (5 N, 8 mL)
  3. additionDilute the mixture with DCM
  4. washwash with water and aqueous saturated sodium chloride
  5. customSeparate the organic layer
  6. dry with materialdry over sodium sulfate
  7. filtrationFilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-608ce1f1ecf24ddca4176d14c57e28b8
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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