Hydrogen Bromide → 3-Fluoro-4-hydroxybenzoic acid

HRID 1646473Notes

Reaction equation

HRID 1646473 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>[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

4

Reactant 2

HCID 260Hydrogen BromideHCID 27334013-Fluoro-4-methoxybenzoic acid

Product 1

HCID 1604563-Fluoro-4-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Next, the 3-fluoro-4-methoxybenzoic acid (IV) was digested with HBr (20 ml) and glacial acetic acid (40 ml) overnight. Most of the acetic acid was distilled off and the remaining mixture was diluted with water. The precipitated benzoic acid was extracted in ether; the ether layer was dried, filtered and rotary evaporated to produce 11.0 g of the 3-fluoro-4-hydroxybenzoic acid (V).

Workup

  1. distillationMost of the acetic acid was distilled off
  2. additionthe remaining mixture was diluted with water
  3. extractionThe precipitated benzoic acid was extracted in ether
  4. dry with materialthe ether layer was dried
  5. filtrationfiltered
  6. customrotary evaporated

Sources & evidence

ORD record
ord-6623deb0f5594901b7121407ed7484b7
Source dataset
uspto-grants-1993_01
Patent number
US05180520

Reaction notes

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