Hydrogen Bromide → 2-(3,4-Dichlorophenyl)-2-oxoacetaldehyde

HRID 1881523Notes

Reaction equation

HRID 1881523 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([Cl:11])[CH:5]=1)=[O:3].Br.[OH2:13]>CS(C)=O>[Cl:11][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH:1]=[O:13])[CH:9]=[CH:8][C:7]=1[Cl:10]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 75841Ethanone, 1-(3,4-dichlorophenyl)-

Product 1

HCID 2754012-(3,4-Dichlorophenyl)-2-oxoacetaldehydeYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

3,4-dichloroacetophenone (5.39 mmol, 1.02 g) was dissolved in dimethyl sulfoxide (13 mL), and 48% hydrobromic acid (1.83 mL) was gradually added at room temperature. The mixture was stirred overnight at 60° C., and then the reactor was cooled to room temperature. The reaction solution was poured into water (50 mL) at 0° C. and stirred for about 1 hour. The precipitated solid was recovered by filtration, washed with water and dried by means of a vacuum pump to give the desired product as a pale yellow solid (0.780 g, yield 71%).

Workup

  1. temperaturethe reactor was cooled to room temperature
  2. stirringstirred for about 1 hour
  3. filtrationThe precipitated solid was recovered by filtration
  4. washwashed with water
  5. customdried by means of a vacuum pump

Sources & evidence

ORD record
ord-b54e58a078a843a395eb3bc77bf825d1
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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