Water → HCID 67963110, compound

Participants

Reaction Steps

266 mg (0.56 mmol) of N-{2-[bis(phenylsulphanyl)methyl]-3,4-dihydronaphthalen-1(2H)-ylidene}-4-fluoroaniline are dissolved in 50 ml of toluene, 0.26 ml (0.26 mmol of a titanium(IV) tetrachloride solution (1 M in dichloromethane) is added a little at a time at 25° C. and the mixture is stirred for 1 h. 431 mg (2.83 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 5 ml of dichloromethane are added, and this mixture is poured into water and extracted with ethyl acetate. After washing with saturated aqueous sodium chloride solution, the organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on RP18 (mobile phase: acetonitrile/water) gives 84 mg of 4-fluoro-N-[(2E)-2-[(phenylsulphanyl)methylene]-3,4-dihydronaphthalen-1(2H)-ylidene]aniline.

Provenance & Evidence