4-Acetylbenzoic Acid → 4-(2-bromoacetyl)benzoic Acid

HRID 18202Notes

Reaction equation

HRID 18202 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:13]Br>C(O)(=O)C>[Br:13][CH2:2][C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 114704-Acetylbenzoic AcidHCID 24408Bromine

Product 1

HCID 27568364-(2-bromoacetyl)benzoic AcidYield 36.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Acetylbenzoic acid (186 mg, 1.14 mmol) was dissolved in warm acetic acid (5 mL) and treated with bromine (58 mL, 1.14 mmol). The solution was stirred overnight before being cooled on ice. The resulting solid was filtered, washed with 1:1 methanol/water (3×10 mL) and dried in vacuo to provide 4-(2-bromoacetyl)benzoic acid as a white solid (102 mg). 1H NMR (200 MHz, DMSO-d6) δ 8.07 (s, 4H), 4.98 (s, 2H).

Workup

  1. temperaturebefore being cooled on ice
  2. filtrationThe resulting solid was filtered
  3. washwashed with 1:1 methanol/water (3×10 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-0af5f95e95df461a81a9be320fefe755
Source dataset
uspto-grants-2010_06
Patent number
US07741349B2

Reaction notes

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