Allyl bromide → HCID 118590516, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Indium powder (27 g, 235 mmol), S-tert-butyl sulfinamide (26.3 g, 216 mmol), 5-fluoro-2-((tetrahydrofuran-3-yl)oxy)benzaldehyde (38.0 g, 181 mmol) and Ti(OEt)4 (61.8 g, 271 mmol) in THF (380 mL) was refluxed for 2 h. Reaction mass was cooled to 0° C. and added 3-bromoprop-1-ene (28.4 g, 235 mmol) slowly for a period of 30 min. Reaction mass was heated to reflux for 16 h, cooled to room temperature and diluted with water (1.0 L), the hazy solution was filtered through celite bed and the solids were washed with ethyl acetate (1.0 L). The filtrate was extracted with ethyl acetate (600 ml). The combined organic phases were washed with water and brine which was dried over Na2SO4 and concentrated to get the desired product as viscous liquid. This was purified over 60-120 mesh silica using 50-60% ethyl acetate and hexane as an eluent to get the pure product (30 g, yield: 47%). MS (ESI): m/z 356.45 (M+H)

Provenance & Evidence