methyl 1-(2-bromophenyl)cyclopropane-1-carboxylate synthesis

Yield:1379317-16-4 76%

Reaction Conditions:

with hydrogenchloride in water at 20; for 40 h;Reflux;

Steps:

(a) Methyl 1-(2-bromophenyl)cyclopropanecarboxylate (14)

(a) Methyl 1-(2-bromophenyl)cyclopropanecarboxylate (14)A solution of 1-(2-bromophenyl)cyclopropanecarboxylic acid (500 mg, 2.07 mmol) inMeOH (10 mL) was treated with a solution of concentrated aqueous HCI (0.5 mL).The resulting mixture was stirred for 16 hours at room temperature and then heated to reflux and stirred for a further 24 hours. The volatiles were evaporated and the residue was dissolved in EtOAc. The organic layer was washed with saturated solution of NaHCO3, brine and then dried over MgSO4. The solvent was removed invacuo to give the title compound 14 (400 mg, 76%) as an orange oil; 1H NMR (400 MHz, ODd3) O 7.60-7.54 (m, 1H), 7.32-7.24 (m, 2H), 7.15 (m, 1H), 3.63 (5, 3H), 1.75 (d, J= 3.1 Hz, 2H), 1.21 (q, J= 4.0 Hz, 2H).

References:

WO2014/26243,2014,A1 Location in patent:Page/Page column 86