1-fluoro-4-methylsulfanylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-fluorothioanisole (19c) (4 g, 28.13 mmol), anhydrous aluminium chloride (8.40 g, 63.02 mmol) and carbon disulphide (89 ml) was heated at reflux under argon atmosphere, and acetic arhydride (2.65 ml, 28.07 mmol) was added dropwise in 2 h. After refluxing for 24h, the solution was poured into crushed ice, water (62.48 ml) and concentrated hydrochloric acid (2.68 ml). The organic phase was separated and water extracted with dichloromethane (3×30 ml), the organic layers were washed with brine, dried and concentrated. The oily residue was chromatographed (50% petroleum ether 40-60° in dichloromethane) to afford 20c (2.98 g) as a colourless crystalline solid, mp 82.0-84.3° C. (58% yield). 1H NMR (CDCl3) δ7.49-7.43 (dd, 1H, J=9.23, 2.44 Hz); 7.29-7.11 (m, 2H); 2.57 (s, 3H); 2.39 (s, 3H). was heated at reflux under argon atmosphere the solution was poured The organic phase was separated water extracted with dichloromethane (3×30 ml) the organic layers were washed with brine dried concentrated The oily residue was chromatographed (50% petroleum ether 40-60° in dichloromethane)