Hydrogen Bromide → 3-Bromo-4-hydroxyphenylacetic acid

HRID 1919964Notes

Reaction equation

HRID 1919964 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8]C.Br>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 1366153-Bromo-4-methoxyphenylacetic acid

Product 1

HCID 27696283-Bromo-4-hydroxyphenylacetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Bromo-4-methoxyphenylacetic acid (1.3 g, 5.6 mmol) was heated in a solution of hydrogen bromide (3 mL) and acetic acid (3 mL) at 100° C. overnight. The mixture was then partitioned between EtOAc and H2O, and the aqueous layer was separated and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customThe mixture was then partitioned between EtOAc and H2O
  2. customthe aqueous layer was separated
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dc38eae3efb649b296de5401ff7bc39b
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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