Ethyl 3-bromo-5-(trifluoromethyl)benzoate synthesis

Yield: 95%

Reaction Conditions:

with sulfuric acidReflux;

Steps:

75
5.20g of 3-bromo-5-(trifluoromethyl)benzoic acid (19.3 mmol) were dissolved in 80 mL of ethanol and 5.27 ml of concentrated sulphuric acid were added and the reaction mixture was refluxed overnight. The solvent vas evaporated under vacuum and the residue was partitioned between water and ethyl acetate. The organic phase was separated, washed twice with water and with brine, dried over magnesium sulphate, filtered and evaporated. 5.43g (95%) of the title compound were obtained. ¹H NMR (200 MHz, CHLOROFORM-D) ppm 1.4 (t, J=7.2 Hz, 3 H) 4.4 (q, J=7.3 Hz, 2 H) 7.9 (s, 1 H) 8.2 (s, 1 H) 8.4 (s, 1 H) HPLC/MS (10 min) retention time 7.32 min. LRMS: m/z 298 (M+1)

References:

Almirall, S.A. EP2196465, 2010, A1 Location in patent:Page/Page column 51; 52