3,4-Dichlorophenol → 4-(3-Bromopropoxy)-1,2-dichlorobenzene

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,4-dichlorophenol (499.4 g. 3.06 moles), 1,3-dibromopropane (2424 ml, 12 moles), 24% sodium hydroxide (613 g, 3.83 moles), and 5 g of tetrabutylammonium hydrogen sulfate were stirred and heated at 50-70° C. for 2 h. The temperature was raised to 80° and heating was continued for 16 hr more. After cooling the lower phase was separated and excess dibromopropane was removed on a rotary evaporator. The residue was distilled through a short vigreux column at 1 mm vacuum. A total of 870 g (87.3%) of product was collected at 125-135° C. 1H-NMR (CDCl3) & 2.23 (m, 2H), 3.50 (t, 2H), 4.02 (t, 2H), 6.7-7.2 (m, 4H).

Provenance & Evidence