Oxalyl chloride → Benzeneacetyl chloride, 4-bromo-

HRID 375266Notes

Reaction equation

HRID 375266 reaction equation
C1[C:6](=[O:7])[CH2:5][C:4]2[CH:8]=[CH:9][C:10]([Br:12])=[CH:11][C:3]=2C1.BrC1C=CC(CC(O)=O)=CC=1.C(Cl)(=O)C([Cl:27])=O>C(Cl)Cl.CN(C)C=O>[Br:12][C:10]1[CH:9]=[CH:8][C:4]([CH2:5][C:6]([Cl:27])=[O:7])=[CH:3][CH:11]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 74654Benzeneacetic acid, 4-bromo-HCID 27335536-Bromo-2-tetralone

Product 1

HCID 181552Benzeneacetyl chloride, 4-bromo-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The synthesis of 6-bromo-β-tetralone is accomplished by dissolving 4-bromophenylacetic acid in methylene chloride and dimethyl formamide, under nitrogen. Oxalyl chloride is added and the mixture is stirred under a positive nitrogen atmosphere to produce the 4-bromophenylacetyl chloride, at a yield which typically is better than 99%.

Sources & evidence

ORD record
ord-7f3a4cae56e547278ded5b9ff5e16f90
Source dataset
uspto-grants-1996_01
Patent number
US05484923

Reaction notes

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