3-Bromo-5-isopropoxybenzoic acid synthesis

Yield:1119779-04-2 100%

Reaction Conditions:

Stage #1: 3-bromo-5-isopropoxy-benzonitrilewith sodium hydroxide;water in ethanol; for 2 h;Heating / reflux;
Stage #2: with hydrogenchloride in water;

Steps:

11.B; 4

To a solution of 3-bromo-5-isopropoxy-benzonitrile (6.0 g, 24.78 mmol) in EtOH (80 ml) was added water (8.0 ml), followed by 50% NaOH (6.52 ml, 123.91 mmol). The reaction mixture was then refluxed for 2 hrs. concentrated down, re-dissolved in water, acidified with HCL extracted with EtOAc. The EtOAc layer was separated, dried over MgSO₄, filtrated, and concentrated to afford the final product 3-bromo-5-isopropoxy-benzoic acid (6.36 g. 100%). ¹H NMR (300 MHz₅ DMSO-^): δ 13.31 (s, IH), 7.56 (s, 1 H), 7.36 (m, 2H), 4.70 (m, 2H), 1.25 (d, J= 6.0 Hz, 6H). LC-MS m/z = 260.4 [ClOHl lBrO3 + H]⁺.

References:

WO2009/23718,2009,A2 Location in patent:Page/Page column 143-144