2-(4-chlorophenoxy)benzaldehyde

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

Procedure: The crude aldehyde from step 1 (23.3 g, 0.10 mmol) was dissolved in dichloromethane (500 mL), and m-chloroperbenzoic acid (70%, 50.0 g, 0.20 mmol) and sodium bicarbonate (25.2 g, 0.30 mmol) were added. The resulting heterogeneous mixture was stirred and heated under reflux for 2 h and then quenched with an aqueous solution of sodium sulfite (0.5 M, 500 mL). After stirring at 25° C. for 30 min, the organic phase was separated and the aqueouse phase was extracted with dichloromethane (2×200 mL). The combined organic phases were washed with a saturated solution of sodium bicarbonate (2×200 mL), dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel, eluting with an 8:2 mixture of hexane and ethyl acetate to give the title phenol. heated under reflux for 2 h quenched with an aqueous solution of sodium sulfite (0.5 M, 500 mL) After stirring at 25° C. for 30 min the organic phase was separated the aqueouse phase was extracted with dichloromethane (2×200 mL) The combined organic phases were washed with a saturated solution of sodium bicarbonate (2×200 mL) dried over magnesium sulfate concentrated The residue was chromatographed on silica gel eluting with an 8:2 mixture of hexane and ethyl acetate

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A heterogeneous mixture of 4-chlorophenol (14.1 g, 0.11 mmol), 4-fluorobenzaldehyde 12.4 g, 0.1 mmol) and CS2CO3 (65.0 g, 0.20 mmol) in DMF (400 mL) was stirred at 90° C. for 6 h. The reaction mixture was poured into water (1.2 L) and extracted with ethyl acetate (2×200 mL). The organic phase was washed with water (2×100 mL), dried over magnesium sulfate and concentrated to give essentially pure 4-chlorophenoxybenzaldehyde, which was used directly in the next step. extracted with ethyl acetate (2×200 mL) The organic phase was washed with water (2×100 mL) dried over magnesium sulfate concentrated

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A heterogeneous mixture of 4-chlorophenol (14.1 g, 0.11 mmol), 4-fluorobenzaldehyde 12.4 g, 0.1 mmol) and Cs2CO3 (65.0 g, 0.20 mmol) in DMF (400 mL) was stirred at 90° C. for 6 h. The reaction mixture was poured into water (1.2 L) and extracted with ethyl acetate (2×200 mL). The organic phase was washed with water (2×100 mL), dried and concentrated to give essentially pure 4-chlorophenoxybenzaldehyde, which was used directly for the next step. extracted with ethyl acetate (2×200 mL) The organic phase was washed with water (2×100 mL) dried concentrated