Boron tribromide → 3-Hydroxyphenacyl bromide

HRID 1348569Notes

Reaction equation

HRID 1348569 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]C)[CH:6]=1)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 101294Bromomethyl 3-methoxyphenyl ketone

Product 1

HCID 69172063-Hydroxyphenacyl bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-bromo-1-(3-methoxy-phenyl)-ethanone (Aldrich, 3.44 g, 15 mmol) in methylene chloride (20 mL) at −10° C., boron tribromide (Aldrich, 16.5 mmol, 1M solution in CH2Cl2, 16.5 mL) was added slowly and the mixture was stirred for 1.5 hours. The reaction was quenched with ice water and the organic layer was separated. The aqueous layer was extracted with EtOAc and the extracts were combined and dried with sodium sulfate. Removal of solvent gave a greenish solid which was purified by chromatography (EtOAc/Hexane, 25%) gave an off-white solid. 770 mg, 24%. The compound was used directly for the next step.

Workup

  1. customThe reaction was quenched with ice water
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialdried with sodium sulfate
  5. customRemoval of solvent
  6. customgave a greenish solid which
  7. customwas purified by chromatography (EtOAc/Hexane, 25%)
  8. customgave an off-white solid

Sources & evidence

ORD record
ord-3cd0f38a4cc4498095a75fb8e2f3d5a2
Source dataset
uspto-grants-2007_05
Patent number
US07211576B2

Reaction notes

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