Boron tribromide → 3-Hydroxyphenacyl bromide

HRID 2298596Notes

Reaction equation

HRID 2298596 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 bromideYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-1-(3-methoxyphenyl)ethan-1-one (2 g, 8.7 mmol) was taken in a round bottomed flask equipped with magnetic stir bar. The flask was put under a N2 atmosphere and CH2Cl2 was introduced into the flask. The resulting solution was cooled in a dry ice acetone bath and BBr3 (27 mL, 1M in CH2Cl2) was introduced dropwise. The resulting solution was allowed to warm up to room temperature over-night. The solvents were removed under vacuum and the residue was purified by passing through a short pad of silica gel (50 g) to give 1.3 g (69%) of 2-bromo-1-(3-hydroxyphenyl)ethan-1-one as an oil. 1H-NMR (CDCl3; 300 MHz) δ4.47 (s, 2H), 6.21 (s, 1H), 7.08-7.19 (m, 1H), 7.23-7.48 (m, 1H), 7.52-7.82 (m, 2H).

Workup

  1. customequipped with magnetic stir bar
  2. temperatureThe resulting solution was cooled in a dry ice acetone bath
  3. customThe solvents were removed under vacuum
  4. customthe residue was purified

Sources & evidence

ORD record
ord-1672ebe1c6e9484bbab0213c9fc0110c
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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