3,4-Dichlorophenol → HCID 13102700, compound

Participants

Reaction Conditions

Reaction Steps

To 44.9 g of t-BuOK in 250 ml of DMSO was added 65.2 g of 3,4-dichlorophenol in 50 ml of DMSO causing a temperature rise to between 65°-70° C. To this warm solution was added 2-chloro-5-nitropyridine (63.4 g) which raised the temperature to 90° C. The mixture was stirred without heating until the temperature dropped to 40° C. (~1 hr). The reaction mixture was poured into 1 kilogram (kg) of ice-water and the solid collected by filtration. The solid was dissolved in CH2Cl2, dried over Na2CO3, treated with charcoal, redried over MgSO4 and then filtered. The CH2Cl2 solution was concentrated to 250 ml, then diluted to 700 ml with hexane and allowed to stand overnight. From this solution, a crystalline material was collected by filtration and 94.8 g of 2-(3,4-dichlorophenoxy)-5-nitropyridine obtained, m.p. 101°-102.5° C.

Provenance & Evidence