1-chloro-2-fluoro-3-phenylmethoxybenzene

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

Procedure: A mixture of 3-chloro-2-fluorophenol (1.5 g, 10.2 mmol), benzyl bromide (1.71 g, 10.0 mmol) and sodium carbonate (1.10 g, 10.38 mmol) in 20 mL ethylene glycol dimethyl ether and 10 mL H2O was stirred at rt for 36 h. The reaction mixture was charged with 20 mL 1N KOH and 50 mL diethyl ether. The organic layer was separated, washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford the title compound as a white solid which was used without further purification. 1H NMR (CDCl3, 400 MHz) δ 5.16 (s, 2Hs) 6.86-7.03 (m, 3Hs) 7.31-7.48 (m, 5Hs). The organic layer was separated washed with brine dried over sodium sulfate concentrated in vacuo

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

Procedure: A mixture of 3-chloro-2-fluorophenol (1.5 g, 10.2 mmol), benzyl bromide (1.71 g, 10.0 mmol) and sodium carbonate (1.10 g, 10.38 mmol) in 20 mL ethylene glycol dimethyl ether and 10 mL H2O was stirred at rt for 36 h. The reaction mixture was charged with 20 mL 1N KOH and 50 mL diethyl ether. The organic layer was separated, washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford the title compound as a white solid which was used without further purification. 1H NMR (CDCl3, 400 MHz) δ 5.16 (s, 2Hs) 6.86-7.03 (m, 3Hs) 7.31-7.48 (m, 5Hs). The organic layer was separated washed with brine dried over sodium sulfate concentrated in vacuo

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

Procedure: A mixture of 3-chloro-2-fluorophenol (1.5 g, 10.2 mmol), benzyl bromide (1.71 g, 10.0 mmol) and sodium carbonate (1.10 g, 10.38 mmol) in 20 mL ethylene glycol dimethyl ether and 10 mL H2O was stirred at rt for 36 h. The reaction mixture was charged with 20 mL 1N KOH and 50 mL diethyl ether. The organic layer was separated, washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford the title compound as a white solid which was used without further purification. 1H NMR (CDCl3, 400 MHz) δ 5.16 (s, 2Hs) 6.86-7.03 (m, 3Hs) 7.31-7.48 (m, 5Hs). The organic layer was separated washed with brine dried over sodium sulfate concentrated in vacuo