Boron tribromide → 2-Bromo-5-hydroxybenzaldehyde

HRID 1914282Notes

Reaction equation

HRID 1914282 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10]C)=[CH:6][C:3]=1[CH:4]=[O:5].B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 3444802-Bromo-5-methoxybenzaldehyde

Product 1

HCID 3871792-Bromo-5-hydroxybenzaldehydeYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-bromo-5-methoxy-benzaldehyde (10 g, 31.25 mmol) in dichloromethane (30 ml) at −78° C. is added BBr3 (25 g, 93.75 mmol) and allowed to warm to room temperature. After 2 h, the reaction is quenched with water and extracted with ethyl acetate. The combined organic layers are washed with water, brine, dried and purified by the column chromatography to afford 3.6 g of the titled compound.

Workup

  1. customthe reaction is quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with water, brine
  4. customdried
  5. custompurified by the column chromatography

Sources & evidence

ORD record
ord-2f200b2ada524a3b9700649e0c643a23
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

Loading…