Dichloromethane → Methyl 4-bromo-4-(chlorobenzoyl)butyrate

HRID 567151Notes

Reaction equation

HRID 567151 reaction equation
[Br:1]Br.Cl[C:4]1[CH:18]=[CH:17][C:7]([C:8]([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:9])=C[CH:5]=1.Cl[CH2:20][Cl:21]>>[Br:1][CH:10]([C:8](=[O:9])[C:7]1[CH:17]=[CH:18][CH:4]=[CH:5][C:20]=1[Cl:21])[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 10966649Methyl 5-(4-chlorophenyl)-5-oxovalerate

Product 1

HCID 18376473Methyl 4-bromo-4-(chlorobenzoyl)butyrateYield 96%

Procedure

Bromine (46.5 g) was added dropwise to a dichloromethane (400 ml) solution of methyl 4-(4-chlorobenzoyl)butyrate (70.0 g). After stirring for 15 minutes, the reaction mixture was washed with water, dried (MgSO4), and concentrated to obtain methyl 4-bromo-4-(chlorobenzoyl)butyrate (89.5 g, 96%) as an oily substance. NMR (δ ppm in CDCl3): 2.3-2.7(4 H,m), 3.71(3H,s), 5.33(1H,dd,J=8&5.5 Hz), 7.48(2H,d,J=8.5 Hz), 7.98(2H,d,J=8.5 Hz).

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-251a6267e6d94f94b29d6530bb39a5ad
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

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