Boron tribromide → 4,5-Difluoro-2-hydroxybenzaldehyde

HRID 618707Notes

Reaction equation

HRID 618707 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:11]C)[CH:3]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:11])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 154345524,5-Difluoro-2-methoxybenzaldehyde

Product 1

HCID 154345534,5-Difluoro-2-hydroxybenzaldehydeYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.8 g (33.7 mmol) of 4,5-difluoro-2-methoxybenzaldehyde in 400 ml of anhydrous dichloromethane was treated dropwise at -70° while stirring over a period of 10 minutes with 37 ml (37 mmol) of a 1 M boron tribromide solution in dichloromethane. Subsequently, the mixture was stirred at room temperature for 16 hours, poured on to 400 ml of ice-water and the phases were separated. The aqueous phase was extracted once with 400 ml of dichloromethane and the combined organic phases were washed once with 200 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated in a vacuum. The crude product obtained was purified by column chromatography on silica gel (hexane/ethyl acetate 4:1). There were obtained 5.05 g (94%) of 4,5-difluoro-2-hydroxybenzaldehyde as a white solid with m.p. 64°.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted once with 400 ml of dichloromethane
  3. washthe combined organic phases were washed once with 200 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in a vacuum
  6. customThe crude product obtained
  7. customwas purified by column chromatography on silica gel (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-0dbfcc55ff644c68aed3b2a933a507bd
Source dataset
uspto-grants-1999_09
Patent number
US05955495

Reaction notes

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