Ethyl Acetate → Methyl 3-bromocinnamate, predominantly trans
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]=1Participants
3
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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