Methanol → 3-Chloro-N-(3,5-difluoro-phenyl)-5-hydroxy-N-propyl-benzamide

HRID 2268585Notes

Reaction equation

HRID 2268585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([O:22]C)[CH:21]=1)[C:5]([N:7]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)[CH2:8][CH2:9][CH3:10])=[O:6].B(Br)(Br)Br.CO>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([OH:22])[CH:21]=1)[C:5]([N:7]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)[CH2:8][CH2:9][CH3:10])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 183489633-chloro-N-(3,5-difluoro-phenyl)-5-methoxy-N-propyl-benzamide

Product 1

HCID 183488623-Chloro-N-(3,5-difluoro-phenyl)-5-hydroxy-N-propyl-benzamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-chloro-N-(3,5-difluoro-phenyl)-5-methoxy-N-propyl-benzamide (0.164 g) in anhydrous dichloromethane (5 ml) at −78° C. was added 1M boron tribromide solution in dichloromethane (3.5 ml). The reaction mixture was stirred at this temperature for 15 min. The reaction was allowed to warm to room temperature, and after 3.5 h the reaction was cooled to −78° C. and methanol (6 ml) added. The reaction was allowed to rewarm to room temperature and the solvent removed in vacuo. The residue was purified by flash column chromatography eluting with cyclohexane:ethyl acetate (3:1 v/v) to give the title compound as a colourless oil (0.110 g).

Workup

  1. temperatureafter 3.5 h the reaction was cooled to −78° C.
  2. customto rewarm to room temperature
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by flash column chromatography
  5. washeluting with cyclohexane:ethyl acetate (3:1 v/v)

Sources & evidence

ORD record
ord-2328b7af8c754c7db6232107dd6f2f10
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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