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

HRID 2235060Notes

Reaction equation

HRID 2235060 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-869963457acf4e75b2ecbd6ba803ced1
Source dataset
uspto-grants-2010_05
Patent number
US07714003B2

Reaction notes

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