Isobutylene → HCID 70496195, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-5-fluoro-benzoic acid methyl ester (12.1 g, 71.4 mmol), 3-bromo-benzaldehyde (13.2 g, 71.4 mmol) and ytterbium(III) triflate hydrate (4.4 g, 71.4 mmol) in acetonitrile (200 mL) was cooled to 0° C. in a sealed reaction bottle. Then a cooled solution of isobutene (28 g, 500 mmol) was added into. The reaction mixture was heated to 90° C. and stirred for 12 h. The solvent was removed in vacuo and the residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (20% ethyl acetate/hexanes) to afford 2-(3-bromo-phenyl)-6-fluoro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (16 g, 57%) as a white solid: MS (ESI) M+1=392.1.

Provenance & Evidence