Bromine → Methyl 4-(bromoacetyl)benzoate

HRID 218084

Reaction equation

HRID 218084 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[Br:14]Br>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH2:11][Br:14])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 137990Methyl 4-acetylbenzoate

Product 1

HCID 13612771Methyl 4-(bromoacetyl)benzoateYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-acetyl-benzoic acid methyl ester (8.4 mmol) in acetic acid (20 mL) was added bromine (8.4 mmol). The reaction was stirred at RT for 2 h over which time the red colour disappeared and an off white precipitate formed. The product was collected by filtration and washed with cold methanol/water (200 mL 1:1) to yield a white powder (55%). 1H NMR (400 MHz, CDCl3) 3.98 (3H, s), 4.20 (2H, s), 8.02 (2H, d, J=8 Hz), 8.18 (2H, d, J=8 Hz).

Workup

  1. customan off white precipitate formed
  2. filtrationThe product was collected by filtration
  3. washwashed with cold methanol/water (200 mL 1:1)

Sources & evidence

ORD record
ord-2a02c8f46c20453180a1b5fd03a9427d
Source dataset
uspto-grants-2012_06
Patent number
US08198283B2

Linked notes

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