Acetic Acid → N-(2-bromo-4-(trifluoromethyl)benzyl)-2',4'-dichloro-[1,1'-biphenyl]-4-amine

HRID 405144Notes

Reaction equation

HRID 405144 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Br:15][C:16]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:17]=1[CH:18]=O.[Cl:28][C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=1[C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1.CC(O)=O>CCOC(C)=O.ClCCCl>[Br:15][C:16]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:17]=1[CH2:18][NH:42][C:39]1[CH:38]=[CH:37][C:36]([C:30]2[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:29]=2[Cl:28])=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 30203732-Bromo-4-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 99647252',4'-Dichloro-[1,1'-biphenyl]-4-amine

Product 1

HCID 86674248N-(2-bromo-4-(trifluoromethyl)benzyl)-2',4'-dichloro-[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid NaBH(OAc)3 (39 mg, 1.9 mmol) was added to a DCE solution (3 mL) of 2-bromo-4-(trifluoromethyl)benzaldehyde (235 mg, 0.9 mmol), 2′,4′-dichloro-[1,1-biphenyl]-4-amine (233 g, 1.0 mmol), and AcOH (0.21 mL, 3.7 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with EtOAc washed with water and brine, dried (Na2SO4), dry-packed onto silica gel and purified via column chromatography to yield the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry-packed onto silica gel and purified via column chromatography

Sources & evidence

ORD record
ord-8b6644c6bc9e4121ba9cb39d95026e5a
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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