Dichloromethane → ethyl (1R,2R)-2-(4-bromophenyl)cyclopropanecarboxylate

HRID 1392692Notes

Reaction equation

HRID 1392692 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH2:15](Cl)Cl>CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:6]2[CH2:15][C@H:7]2[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 141107Ethyl 4-bromocinnamate

Product 1

HCID 66578655ethyl (1R,2R)-2-(4-bromophenyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of ethyl 4-bromocinnamate and Pd(OAc)2 (0.05 eq) in methylene chloride (1M) at 0° C. was added dropwise a solution of CH2N2 in ether until the reaction was completed by NMR analysis. The mixture was filtered through a plug of silica gel and concentrated to afford the title compound as an oil.

Workup

  1. filtrationThe mixture was filtered through a plug of silica gel
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-daf18f7dddce4ef5916e8ba4ccc0f87b
Source dataset
uspto-grants-2008_03
Patent number
US07342024B2

Reaction notes

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