Thionyl Chloride → 3-(Bromophenyl)-2-n-propylpropionyl chloride

HRID 1259Notes

Reaction equation

HRID 1259 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([CH2:13][CH2:14][CH3:15])[C:10](O)=[O:11].S(Cl)([Cl:18])=O>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([CH2:13][CH2:14][CH3:15])[C:10]([Cl:18])=[O:11]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 218384192-(2-Bromobenzyl)pentanoic acid

Product 1

HCID 218384183-(Bromophenyl)-2-n-propylpropionyl chloride

Procedure

A 500-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a thermometer and a NaOH trap was charged with 277 mmol of 3-(2-bromophenyl)-2-propylpropionic acid and 200 ml of thionyl chloride, and the mixture was heated under reflux for 2 hours. Then, the excess thionyl chloride was removed by a single distillation, and the distillation of the residue under reduced pressure gave 77.4 g of a crude product having a boiling point of 130° to 135° C./1 mmHg as a pale brown transparent liquid. This acid chloride was used in the next reaction without further purification

Workup

  1. customA 500-ml three-necked round flask equipped with a stirring bar
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customThen, the excess thionyl chloride was removed by a single distillation
  5. distillationthe distillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-6f4401e734f84a7c9ca25250dd8869e3
Source dataset
uspto-grants-1998_03
Patent number
US05723640

Reaction notes

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