Boron tribromide dichloromethane → N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-4-phenylbenzamide

HRID 644486Notes

Reaction equation

HRID 644486 reaction equation
B(Br)(Br)Br.ClCCl.[F:8][C:9]([F:38])([F:37])[C:10]1[CH:11]=[C:12]([NH:20][C:21](=[O:36])[C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:24][C:23]=2[O:34]C)[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1>ClCCl.C(OCC)(=O)C>[F:8][C:9]([F:37])([F:38])[C:10]1[CH:11]=[C:12]([NH:20][C:21](=[O:36])[C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:24][C:23]=2[OH:34])[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1

Participants

5

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 57459277N-[3,5-bis(trifluoromethyl)phenyl]-2-methoxy-4-phenylbenzamide

Product 1

HCID 57459276N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-4-phenylbenzamideYield 71.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1M Boron tribromide-dichloromethane solution (0.71 mL, 0.71 mmol) was added to a solution of N-[3,5-bis(trifluoromethyl)phenyl]-2-methoxy-4-phenylbenzamide (100 mg, 0.24 mmol) in dichloromethane (5 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1) to give the title compound (69.3 mg, 71.6%) as a white powder.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe residue obtained by evaporation of the solvent under reduced pressure
  4. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-433a038281f546159344170c537681fe
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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