Benzeneacetic acid, 3,5-dibromo-4-hydroxy-, ethyl ester

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure of Newman and Karnes, J. Org. Chem. 31, 3980 (1966), a mixture of ethyl 3,5-dibromo-4-hydroxyphenylacetate (20 g, 0.06 mol), from Preparation B, N,N-dimethylthiocarbamoyl chloride (10.9 g, 0.088 mol), and 1,4-diazabicyclo[2 2.2]octane (Dabco™) (13.4 g, 0.12 mol) in 250 mL DMF was heated, with stirring, at 70° C. for one hour. The reaction mixture was cooled and the precipitate (Dabco-HCl salt) removed by filtration and washed well with ethyl acetate. The filtrate was concentrated on a rotary evaporator and the solid collected by filtration, washed well with water and dried in vacuum to obtain ethyl 3,5-dibromo-4-(N,N-dimethylthiocarbamoyloxy)phenylacetate (16 g, 0.037 mol, 62% yield), MP: 93°-95° C. (hexane/ethyl acetate). was heated The reaction mixture was cooled the precipitate (Dabco-HCl salt) removed by filtration washed well with ethyl acetate The filtrate was concentrated on a rotary evaporator the solid collected by filtration washed well with water dried in vacuum

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

Procedure: 3,5-Dibromo-4-hydroxyphenylacetic acid (60 g, 0.19 mol), from Preparation A, was suspended in 1 L of ethanol and 10 mL of concentrated sulfuric acid and heated at reflux overnight. The reaction mixture was cooled, concentrated and the product collected by filtration, washed with water, and dried in a vacuum oven to obtain ethyl 3,5-dibromo-4-hydroxyphenylacetate. at reflux overnight The reaction mixture was cooled concentrated the product collected by filtration washed with water dried in a vacuum oven