Dimethylformamide → Benzenepropanoyl chloride, 2-broMo-

HRID 1825261Notes

Reaction equation

HRID 1825261 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=O.C(Cl)(=O)C([Cl:16])=O.CN(C)C=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([Cl:16])=[O:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 3160103-(2-Bromophenyl)propionic acid

Product 1

HCID 22145269Benzenepropanoyl chloride, 2-broMo-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(2-bromophenyl)propanoic acid (prepared in 2 steps from 2-bromobenzyl bromide, 2.0 g, 8.73 mmole), oxalyl chloride (1.14 ml, 13.1 mmole) and methylene chloride (20 ml) was cooled in an ice bath and N,N-dimethylformamide (34 μL, 0.44 mmole) was added dropwise. The mixture was stirred at room temperature for 3 hours. Concentration in vacuo gave 3-(2-bromophenyl)propanoyl chloride which was taken up in methylene chloride and used in the next step as a crude. Step 2:

Workup

  1. temperaturewas cooled in an ice bath
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-56f350d6841b449db1698056394bf123
Source dataset
uspto-grants-2006_05
Patent number
US07045591B2

Reaction notes

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