Boron tribromide → 2-(2-Bromo-5-hydroxyphenyl)acetonitrile

HRID 885265Notes

Reaction equation

HRID 885265 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[CH2:10][C:11]#[N:12].B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:10][C:11]#[N:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 6396662-(2-Bromo-5-methoxyphenyl)acetonitrile

Product 1

HCID 544192022-(2-Bromo-5-hydroxyphenyl)acetonitrileYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To (2-bromo-5-methoxy-phenyl)-acetonitrile (2.6 g, 11.5 mmol) in CH2Cl2 (20 mL) at 0° C. under N2 was added boron tribromide (1M in CH2Cl2; 25.4 mL, 25.4 mmol). The mixture was stirred for 15 minutes at 0° C., and at mom temperature overnight. After a work-up with H2O and CH2Cl2, the crude material was purified by silica gel chromatography to give the desired product as a white solid (1.5 g).

Workup

  1. customat mom temperature overnight
  2. customAfter a work-up with H2O and CH2Cl2, the crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-400ec52be88c4c6c905335bd1947448c
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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