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

HRID 861020Notes

Reaction equation

HRID 861020 reaction equation
[CH2:1]([O:3][C:4](=[O:14])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[CH3:2].[CH2:15]1COCC1>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:3][C:4]([C@@H:5]1[CH2:15][C@H:6]1[C:7]1[CH:8]=[CH:9][C:10]([Br:13])=[CH:11][CH:12]=1)=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 688115Ethyl trans-4-Bromocinnamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

To a solution of E-3-(4-bromo-phenyl)-acrylic acid ethyl ester and Pd(OAc)2 (0.05 eq.) in THF (0.2M) was added portionwise CH2N2 until the reaction was completed. NMR of aliquots monitored the reaction. The resulting mixture was concentrated and filtered on celite to afford the title compound as an oil.

Workup

  1. customthe reaction
  2. concentrationThe resulting mixture was concentrated
  3. filtrationfiltered on celite

Sources & evidence

ORD record
ord-0a126e1545b940fdb057550d8c3a0fa8
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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