Sodium Hydroxide → 3-(4-broMophenyl)-2,2-diMethylpropanoic acid

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Reaction Steps

1-bromo-4-(2-methoxycarbonyl-2-methylpropyl)benzene (7.79g) was dissolved in methanol (60 ml) and 2M aqueous sodium hydroxide solution (30 ml) was added. The solution was heated to reflux for 2 hours then cooled. The volume was reduced to ~25 ml by evaporation and the residue extracted with ethyl acetate (15 ml) then acidified with 2M hydrochloric acid and re-extracted with ethyl acetate (3×25 ml). The combined organic extract of the acidified aqueous phase was dried (MgSO4) and evaporated to give 1-bromo-4-(2-carboxy-2-methylpropyl)benzene (6.1 g); 1H NMR (d6 -DMSO): 1.08 (s, 6 H), 2.78 (s, 2 H), 7.11 (m, 2 H), 7.46 (m, 2 H); mass spectrum (CI+) 256 (M+H)+.

Provenance & Evidence