Bromine → Methyl 4-(2-bromoacetyl)benzoate

HRID 1405413Notes

Reaction equation

HRID 1405413 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:14]Br>CC(O)=O>[Br:14][CH2:2][C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 137990Methyl 4-acetylbenzoate

Product 1

HCID 13612771Methyl 4-(2-bromoacetyl)benzoateYield 82.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 4-acetylbenzoate (8.91 g, 50.0 mmol) in AcOH (80 mL) was added Br2 (2.71 mL, 52.5 mmol) dropwise. The mixture was stirred at room temperature for 2 h. The mixture was cooled to 0° C. and the solid was filtered. The precipitate was washed with 1:1 MeOH in water and was desiccated to give methyl 4-(2-bromoacetyl)benzoate (10.6 g, 82%) as a tan solid. 1H NMR (400 MHz, CDCl3) δ 8.19-8.12 (m, 2H), 8.04 (d, J=8.5 Hz, 2H), 4.47 (s, 2H), 3.96 (s, 3H).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. filtrationthe solid was filtered
  3. washThe precipitate was washed with 1:1 MeOH in water

Sources & evidence

ORD record
ord-57dece554f9044cf80f361aac0a68bd4
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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