Bromine → Ethyl 4-(3,4-Dimethoxyphenyl)-4-oxo-2-butynoate

HRID 841961Notes

Reaction equation

HRID 841961 reaction equation
Br[CH:2]([CH:8](Br)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].COC1C=C(C(=O)C=CC(OCC)=O)C=CC=1OC.BrBr>C(Cl)Cl>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([C:9](=[O:10])[C:8]#[C:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 24408BromineHCID 22222634Ethyl 2,3-dibromo-4-(3,4-dimethoxyphenyl)-4-oxobutanoateHCID 53400457Ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate

Product 1

HCID 22222587Ethyl 4-(3,4-Dimethoxyphenyl)-4-oxo-2-butynoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The procedure as described above in connection with Intermediate 1 was repeated to prepare ethyl 2,3-dibromo-4-(3,4-dimethoxyphenyl)-4-oxobutanoate (7.3 g, 95%) in the form of a diastereo mixture as a colorless foam (mixing ratio=63:37) from, a solution of ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate (4.8 g, 18 mmol) in methylene chloride (500 ml) and a solution of bromine (1.1 ml) in methylene chloride (100 ml). The diastereo mixture was used in the next reaction without separation.

Workup

  1. customThe diastereo mixture was used in the next reaction without separation

Sources & evidence

ORD record
ord-e3bf59f7b73147d48731b81409b3a59a
Source dataset
uspto-grants-2002_04
Patent number
US06372735B1

Reaction notes

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