Bromine → Ethyl 6-bromo-6-(4-chlorobenzoyl)hexanoate

HRID 2300669Notes

Reaction equation

HRID 2300669 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:9])=[CH:6][CH:5]=1>ClCCl>[Br:1][CH:10]([C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:21][CH:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 11065929Ethyl 7-(4-chlorophenyl)-7-oxoheptanoate

Product 1

HCID 11810554Ethyl 6-bromo-6-(4-chlorobenzoyl)hexanoateYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine(21.1 g) was added dropwise to a dichloromethane solution (200 ml) of ethyl 6-(4-chlorobenzoyl)hexanoate (37.3 g) at room temperature. After stirring for 30 minutes, the reaction mixture was washed with sodium hydrogensulfite, saturated sodium bicarbonate and water in turn. The dichloromethane layer was dried(MgSO4). The solvent was evaporated to give ethyl 6-bromo-6-(4-chlorobenzoyl)hexanoate(47.6 g, quant.) as an oily substance.

Workup

  1. washthe reaction mixture was washed with sodium hydrogensulfite, saturated sodium bicarbonate and water in turn
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-36616594bbb44475a902eccb52f28337
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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