Borane;tetrahydrofuran → 2-(2-Bromo-4-fluorophenyl)-2-methylpropan-1-amine

HRID 558116Notes

Reaction equation

HRID 558116 reaction equation
B.C1COCC1.[Br:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]([CH3:19])([CH3:18])[C:16]#[N:17]>C1COCC1>[Br:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]([CH3:19])([CH3:18])[CH2:16][NH2:17]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 574450632-(2-Bromo-4-fluorophenyl)-2-methylpropanenitrile

Product 1

HCID 574450652-(2-Bromo-4-fluorophenyl)-2-methylpropan-1-amineYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add borane-THF complex (2 M in THF, 10 mL, 20 mmol) to a stirred solution of 2-(2-bromo-4-fluoro-phenyl)-2-methyl-propionitrile (0.8 g, 3.30 mmol) in 10 mL of THF at 0° C. Stir the mixture at 0° C. to RT over the weekend. Quench the reaction with diluted ammonium hydroxide. Extract the product with chloroform. Dry the organic phase over sodium sulfate and concentrate to give the title compound (0.8 g, 99%). MS (ES) m/z 246/248 [M+1]+.

Workup

  1. customQuench
  2. customthe reaction with diluted ammonium hydroxide
  3. extractionExtract the product with chloroform
  4. dry with materialDry the organic phase over sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-e0a86ba2cea449d8aaf894b0330cb5f9
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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