Ethyl Acetate → Methyl 3-bromocinnamate, predominantly trans

HRID 1275387Notes

Reaction equation

HRID 1275387 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1.[C:12](OCC)(=[O:14])C>>[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([O:14][CH3:12])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 186764783-(3-Bromophenyl)-2-propen-1-ol

Product 1

HCID 1482751Methyl 3-bromocinnamate, predominantly transYield 73%

Procedure

The title compound was prepared from trans-3-(3-bromophenyl)-2-propenol by a sequence analogous to that described above for compound (9a) but using D-(-)-diethyl tartrate. Column chromatography (ethyl acetate--light petroleum (b.p. 40-60° C.), 3:7) provided the title compound (73%) as a pale yellow oil. Distilled at 160-185° C. at 0.1 mmHg. using a Kugelrohr short path distillation apparatus as a colourless oil; [α]D25 +37.6 (c=0.020 gml-1, CHCl3).

Sources & evidence

ORD record
ord-4d9fef9211844890b29826ee635256d3
Source dataset
uspto-grants-2000_12
Patent number
US06160120

Reaction notes

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