Hydrogen Bromide → Methyl 4-(2-oxoacetyl)benzoate

HRID 607590Notes

Reaction equation

HRID 607590 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.CS(C)=[O:17]>O>[O:17]=[CH:11][C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:13])=[CH:5][CH:6]=1)=[O:12]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 137990Methyl 4-acetylbenzoate

Product 1

HCID 14276918Methyl 4-(2-oxoacetyl)benzoateYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-acetylbenzoic acid methyl ester (25 g, 0.14 mol) in dimethyl sulfoxide (300 mL) was added slowly a solution of hydrogen bromide in water (48%, 48 mL) at RT with stirring. The mixture was stirred at 60° C. overnight. After cooling it was poured into ice-water. The formed precipitate was collected by filtration and dried in-vacuo to afford the desired product (15.6 g, 79%).

Workup

  1. stirringThe mixture was stirred at 60° C. overnight
  2. temperatureAfter cooling it
  3. filtrationThe formed precipitate was collected by filtration
  4. customdried in-vacuo

Sources & evidence

ORD record
ord-2a0091b2d70c4bafa766246677af1962
Source dataset
uspto-grants-2011_03
Patent number
US07915408B2

Reaction notes

Loading…