1-Naphthoic acid → 4-Chloro-2-methoxy-1-phenoxybenzene

Participants

Reaction Conditions

Reaction Steps

Iodobenzene (7.35 mmol), 4-chloro-2-methoxyphenol (14.7 mmol), Cs2CO3 (32.3 mmol), copper(I) trifluoromethanesulfonate benzene complex (0.735 mmol, 5.0 mol % Cu), ethyl acetate (0.125 mmol, 5.0 mol %), 1-naphthoic acid (32.3 mmol), molecular sieves 4A (1.8 g) and toluene (15 mL) were added to an oven-dried 50 mL two-necked round-bottomed flask. The flask was sealed with a rubber septum, purged with nitrogen, and the temperature raised to 110° C. overnight and monitored by thin layer chromatography. The solution was cooled to room temperature, followed by the addition of 50 mL dichloromethane. The solution was filtered and then washed with a 5% sodium hydroxide aqueous solution. The aqueous layer was then extracted with dichloromethane and the combined organic layers washed with brine (NaCl). The organic phase was dried over anhydrous Mg2SO4 and concentrated under vacuum to give the crude product. Purification by flash chromatography on silica gel afforded the analytically pure compound (3): 1H NMR (300 MHz) (CDCl3): δ 7.35-6.94 (m, 8H), 3.86 (s, 3H).

Provenance & Evidence