Ethyl Acetate → ethyl (1R,2S)-2-(4-bromophenyl)cyclopropane-1-carboxylate

Reaction equation

COC(=O)/[CH:4]=[CH:5]\[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1.[CH3:14][CH2:15][O:16][C:17]([CH3:19])=[O:18]>>[CH2:15]([O:16][C:17]([C@@H:19]1[CH2:4][C@@H:5]1[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)=[O:18])[CH3:14]

Participants

Reactant 2

HCID 8857Ethyl Acetate

HCID 1712253Z-3-(4-Bromo-phenyl)-acrylic acid methyl ester

Product 1

HCID 66578128ethyl (1R,2S)-2-(4-bromophenyl)cyclopropane-1-carboxylate

Procedure

Prepared according to the procedure described in Example 42, Step 1, but using Z-3-(4-Bromo-phenyl)-acrylic acid methyl ester from Step 1 as starting material Flash chromatography (Hex:EtOAc 85:15) afforded the title compound as a oil.

Workup

customPrepared

Sources & evidence

ORD record: ord-957c96b542564d4485e8848da6d762e3
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153968B2

Reaction notes

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