METHYL 5-BROMO-2-HYDROXY-4-METHYLBENZOATE synthesis

Yield: 98.1%

Reaction Conditions:

with bromine in chloroform at 20; for 3 h;

Steps:

Intermediate 14: Methyl 5-bromo-2-hydroxy-4-methylbenzoate (1-14)
To a solution of methyl 2-hydroxy-4-methyl-benzoate (10.6 g, 0.06 mol) in chloroform (20 mL) was added dropwise bromine (3.27 mL, 0.06 mol) at 0°C and the mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure, the residue was neutralized with sodium sulfite solution under ice-cooling, pH 8,and the mixture was extracted with dichloromethane (100 mL x 3). Organic layer was washed with brine solution (50 mL) and dried over Na2SO4 and the solvent was concentrated under vacuum to obtain the crude compound which was further purified by flash chromatography using n-hexane: ethyl acetate (97:3) to afford the title compound. Yield: 15 g (98.1%); ‘H -NMR (CDC13, 400 MHz) ö ppm: 2.38 (s, 3H), 3.94 (s, 3H), 6.88 (s, 1H), 7.96 (s, 1H), 10.58(s, 1H); Mass (mlz): 244.8 (M+H).

References:

SUVEN LIFE SCIENCES LIMITED;NIROGI, Ramakrishna;MOHAMMED, Abdul Rasheed;SHINDE, Anil Karbhari;GAGGINAPALLY, Shankar Reddy;KANCHARLA, Durga Malleshwari;PANDEY, Santosh Kumar;ABRAHAM, Renny;JASTI, Venkateswarlu WO2019/82140, 2019, A1 Location in patent:Page/Page column 22; 23