Methanol → Methyl 3-bromocinnamate, predominantly trans

반응식

S(=O)(=O)(O)O.[Br:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[CH:10]=[CH:11][C:12]([OH:14])=[O:13].[CH3:18]O>>[CH3:18][O:13][C:12](=[O:14])/[CH:11]=[CH:10]/[C:9]1[CH:15]=[CH:16][CH:17]=[C:7]([Br:6])[CH:8]=1

참가 물질

반응물 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 362513-(3-Bromophenyl)acrylic acid

생성물 1

HCID 1482751Methyl 3-bromocinnamate, predominantly trans

실험 절차

Add concentrated sulfuric acid (5.0 mL, 90 mmol) to a solution of 3-bromocinnamic acid (25.0 g, 110 mmol) in MeOH (250 mL). Heat the mixture to reflux for 5 h then cool to room temperature and concentrate under reduced pressure. Dilute the residue with water and extract with EtOAc. Concentrate the combined organic phase under reduced pressure and purify the residue by silica gel chromatography to provide 26 g of trans-3-(3-bromo-phenyl)-acrylic acid methyl ester.