2,6-Dichlorophenol → 2-(2-Bromoethoxy)-1,3-dichlorobenzene

Participants

Reaction Conditions

Reaction Steps

Into a 10 mL round bottom flask was added 2,6-dichlorophenol (326 mg, 2 mmol) and DMF (2 mL). Potassium carbonate (276 mg, 2 mmol, 10 eq) and 1,2-dibromoethane (3.76 g, 20 mmol, 10 eq) was added. The flask was fitted with a reflux condenser and nitrogen inlet and the reaction heated to 100° C. for 2 hours. The mixture was partitioned between water (20 mL) and chloroform (20 mL). The organic layer was separated and the aqueous layer was further extracted with chloroform (3×20 mL). The organic layers were combined, washed twice with 10% sodium carbonate (20 mL) and once with brine (20 mL). The combined organic phase was dried over sodium sulfate and filtered. Solvent was removed under vacuum to leave a brown oil of 2A (264 mg, 49%) which was analytically pure.

Provenance & Evidence