Bromine → 5-Bromo-4-fluoro-2-hydroxybenzoic acid

HRID 17518

Reaction equation

HRID 17518 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[Br:12]Br>C(O)(=O)C>[Br:12][C:10]1[C:2]([F:1])=[CH:3][C:4]([OH:11])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 24408BromineHCID 676614-Fluorosalicylic acid

Product 1

HCID 184681915-Bromo-4-fluoro-2-hydroxybenzoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

4-Fluoro-2-hydroxybenzoic acid (29.01 g, 0.186 mol) was dissolved in acetic acid (290 ml), then a solution of bromine (31.18 g, 0.195 mol) dissolved in acetic acid (15 ml) was gradually dropwise added at room temperature (1 hour). After stirred at 60° C. for 24 hours, this was cooled to room temperature. The reaction liquid was dried to solidness under reduced pressure, the residue was dissolved in methanol (100 ml), and this was poured into water (600 ml). After stirring at room temperature for 15 minutes, the precipitated crystal was washed and collected by filtration, and dried to obtain the entitled compound (35.36 g, 93%) as a colorless solid.

Workup

  1. additionwas gradually dropwise added at room temperature (1 hour)
  2. temperaturethis was cooled to room temperature
  3. customThe reaction liquid
  4. customwas dried to solidness under reduced pressure
  5. dissolutionthe residue was dissolved in methanol (100 ml)
  6. additionthis was poured into water (600 ml)
  7. stirringAfter stirring at room temperature for 15 minutes
  8. washthe precipitated crystal was washed
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-153440b1f9a7449d9fe9b96ed3eeff53
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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