Acetic Acid → 3-Fluoro-4-hydroxybenzoic acid

HRID 2372251Notes

Reaction equation

HRID 2372251 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11]C)[C:5]([OH:7])=[O:6].Br.C(O)(=O)C>O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 27334013-Fluoro-4-methoxybenzoic acid

Product 1

HCID 1604563-Fluoro-4-hydroxybenzoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

98.8 g of 3-fluoro-4-methoxy benzoic acid was mixed with 215 ml of concentrated hydrogen bromide solution and 215 ml of acetic acid and heated under reflux for 34 hours with stirring. Thereafter, the reaction mixture was cooled with water, and the precipitated crystal was filtered to obtain a blackish brown crystal. This crystal was recrystallized with water to obtain 77.73 g (yield: 86%) of a black crystal. Moreover, the use of this crystal itself caused no problem at the subsequent step though it may be changed into white by further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 34 hours
  3. filtrationthe precipitated crystal was filtered
  4. customto obtain a blackish brown crystal
  5. customThis crystal was recrystallized with water

Sources & evidence

ORD record
ord-cd9edc5972054094932e61fba35dd340
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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