Boron tribromide dichloromethane → 4-Chloro-2-(2-phenylethenyl)phenol

HRID 644448Notes

Reaction equation

HRID 644448 reaction equation
B(Br)(Br)Br.ClCCl.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:23]C)=[C:13]([CH:22]=1)[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl.C(OCC)(=O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([OH:23])=[C:13]([CH:14]=[CH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:22]=1

Participants

5

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 685787655-Chloro-2-methoxy-beta-phenylstyrene

Product 1

HCID 685807274-Chloro-2-(2-phenylethenyl)phenolYield 49.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon atmosphere, 1 mol/L boron tribromide/dichloromethane solution (0.5 mL, 0.5 mmol) was added to a solution of 5-chloro-2-methoxy-β-phenylstyrene (80 mg, 0.3 mmol) in dichloromethane (2 mL) at room temperature, and the mixture was stirred for 12 hours. The reaction mixture was diluted with ethyl acetate (15 mL), and after it was washed successively with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1) to give the title compound (34.2 mg, 45.4%) as a white powder.

Workup

  1. washafter it was washed successively with water and brine
  2. dry with materialdried over anhydrous sodium 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=3:1)

Sources & evidence

ORD record
ord-ddae2e34a715429fa32f65a3b9ff0584
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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