Ethanol → 1-(2-Bromoethoxy)-4-iodo-2-methylbenzene

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Reaction Steps

A mixture of 2-methyl-4-iodophenol (5.00 grams), 1,2-dibromoethane (2.76 mL), sodium hydroxide (1.3 grams) and ethanol (100 mL) was stirred at reflux for 5 hours before being poured into ice. The crude solid was dissolved in dichloromethane and washed with 1N NaOH. The organic layer was evaporated in vacuo to give 2-Bromo-1-(2-methyl-4-iodophenoxy)ethane Compound 21a as a tan solid. 1H NMR (CDCl3) δ 6.54 (d, 1H), 4.25 (t, 2H), 3.66 (t, 2H), 2.20 (s, 3H).

Provenance & Evidence