Hydrogen Bromide → 4-Chloro-3-hydroxyphenylacetic acid

HRID 1686375Notes

Reaction equation

HRID 1686375 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[O:12]C.Br>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[OH:12]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 204976552-(4-Chloro-3-methoxyphenyl)acetic acid

Product 1

HCID 30171834-Chloro-3-hydroxyphenylacetic acidYield 93.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The product from step (ii) (12.2 g), HBr (48% aq.) and acetic acid (10 ml) were charged to a flask and heated at reflux for 24 h, cooled then evaporated under reduced pressure. The residue was triturated with ether/isohexane, and then filtered to give the subtitle compound (10.6 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. temperaturecooled
  4. customthen evaporated under reduced pressure
  5. customThe residue was triturated with ether/isohexane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c47ae56e467746e6a83d5b08acb045ab
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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