CYCLOBUTYL 4-THIOMETHYLPHENYL KETONE synthesis

Yield:716341-27-4 91%

Reaction Conditions:

with aluminum (III) chloride in 1,2-dichloro-ethane at -10 - 10; for 0.75 h;

Steps:

3.a Example 3; 1-cyclobutylmethyl-4-methylsulfanyl-benzene; a) cyclobutyl-(4-methylsulfanyl-phenyl)-methanone

Cyclobutane carboxylic acid chloride (4.50g, 38 MMOL) DISSOLVED in DICHLOROETHANE (10 MI) was added dropwise to a COLD (-10°C) suspension OF AICI3 (4. 81g, 38 MMOL) in DICHLOROETHANE (20 ML). To this solution was added METHYLSULFANYL-BENZENE (4.49g, 36 MMOL) at such a rate that the temperature did not exceed 10°C. After the mixture was stirred for 45 min in an ice bath, it was poured on water and extracted with DICHLOROETHANE. The organic phase was separated, washed with water and brine, dried (MGS04) and concentrated in vacuo to yield a crystalline solid (6.78g, 91%). 1H-NMR (CDCl3, 400MHZ) : 7.81-7. 79 (m, J = 6.8 Hz, 2H), 7.27-7. 24 (m, J = 6.8 Hz, 2H), 3.95 (QUINT. , J = 8.5 HZ, 1 H), 2.51 (S, 3H), 2.47-2. 23 (M, 4H), 2.13-2. 03 (M, 1 H), 1.95-1. 86 (m, H) ppm. GC/MS (El) : 206 (M+, 18), 178 (2), 151 (100), 123 (7), 108 (8), 79 (5), 45 (6)

References:

WO2004/56765,2004,A1 Location in patent:Page 7