Boron tribromide → Methyl 2,6-difluoro-4-hydroxybenzoate

HRID 1857901Notes

Reaction equation

HRID 1857901 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([O:12]C)[CH:9]=[C:8]([F:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].B(Br)(Br)Br>>[F:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([F:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 598880Methyl 2,6-difluoro-4-methoxybenzoate

Product 1

HCID 22087431Methyl 2,6-difluoro-4-hydroxybenzoateYield 66.9%

Procedure

To the above methyl 2,6-difluoro-4-methoxybenzoate (90 g) was added boron tribromide (224 g) under cooling, and then the mixture was stirred for 2 hours at room temperature. After the reaction, the reaction mixture was extracted with ethyl acetate (300 ml). The organic layer separated was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was distilled under reduced pressure to give methyl 2,6-difluoro-4-hydroxybenzoate (56 g).

Workup

  1. temperatureunder cooling
  2. customAfter the reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate (300 ml)
  4. customThe organic layer separated
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-fe235a7277e94d0d91dee73be5193684
Source dataset
uspto-grants-2000_11
Patent number
US06149990

Reaction notes

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