Bromine → 6-Bromo-2-fluoro-3-methoxybenzoic acid

HRID 335974

Reaction equation

HRID 335974 reaction equation
[F:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:13]Br>C(O)(=O)C.O>[Br:13][C:7]1[C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[C:10]([O:11][CH3:12])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 33906792-Fluoro-3-methoxybenzoic acid

Product 1

HCID 534387896-Bromo-2-fluoro-3-methoxybenzoic acidYield 83.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To the suspension of 2-fluoro-3-methoxybenzoic acid (20 g, 118 mmol) in Acetic Acid (100 mL) and water (100 mL) at RT, bromine (12.05 mL, 235 mmol) was added dropwise. The reaction mixture was heated for 1 h at 60° C. The reaction was then cooled to RT and white precipitate was filtered. The solid was washed with excess water and dried to give 6-bromo-2-fluoro-3-methoxybenzoic acid (24.68 g, 99 mmol) as a white solid.

Workup

  1. temperatureThe reaction was then cooled to RT
  2. filtrationwhite precipitate was filtered
  3. washThe solid was washed with excess water
  4. customdried

Sources & evidence

ORD record
ord-5a2957c424af4dc5bd8f88bdb10436ce
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Linked notes

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