Bromine → Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-oxo-3-bromobutyrate

HRID 1823752Notes

Reaction equation

HRID 1823752 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12](=[O:20])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][CH:11]=1.[Br:26]Br>CCOCC>[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12](=[O:20])[CH:13]([Br:26])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 21964476Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-oxobutyrate

Product 1

HCID 21964536Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-oxo-3-bromobutyrate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a ice cooled solution of Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-oxobutyrate (Step C, 3 g, 9 mmol) in dry ether (70 ml) was added dropwise bromine (0.7971 g, 9.9 mmol) diluted in ether (30 ml). After 4 hours of stirring, reaction mixture was concentrated and purified by flash chromatography on silica gel column (EtOAc:Hex, 1:4) to provide the title compound.

Workup

  1. customreaction mixture
  2. concentrationwas concentrated
  3. custompurified by flash chromatography on silica gel column (EtOAc:Hex, 1:4)

Sources & evidence

ORD record
ord-53932fafb83945f5921f2092e0e7a1da
Source dataset
uspto-grants-2006_05
Patent number
US07041659B2

Reaction notes

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