Thiophenol → 8-fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one

Participants

Reaction Steps

A solution of 6,8-difluoro-3,4-dihydro-2H-naphthalen-1-one (1.58 kg) in N,N-dimethylacetamide (4.65 liters) was treated with triethylamine (877 g) and thiophenol (954.9 g) at 20° C. and the reaction mixture was stirred for 19 hours. The reaction mixture was treated with heptane (2.38 liters.), followed by water (9.5 liters) and the precipitate was isolated by filtration and the resulting slurry washed with twice with heptane (790 ml each time), three times with water (1.0 liters each time) and five times with cyclohexane (1.0 liters, each time). The slurry was dried to give 8-fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one (1.86 kg, 79% yield) with a purity of 96.2% by HPLC, together with 3.6% yield of the isomer 6-fluoro-8-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one: MP=111.7-112.7° C.; MS (M+1)=273; H1 NMR (300 MHz): δ (DMSO): 1.96 (2H, p, J=6.4 Hz), 2.53 (2H, t, J=6.03 Hz), 2.84 (2H, t, J=6.03 Hz), 6.69 (1H, dd, J=1.51, 12.06 Hz), 6.91 (1H, d, J=1.13 Hz), 7.5-7.61 (5H, m, Phenyl).

Provenance & Evidence