1-bromo-4-(chloromethyl)-2-methylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To flask containing methyl 3-(3-hydroxyphenyl)propanoate (available from Aagile Labs Division of Tyger Scientific) (0.25 g, 1.387 mmol) and cesium carbonate (0.5876 g, 1.804 mmol) in DMF (8 mL), was added 1.2 (0.3654 g, 1.665 mmol). The resulting mixture was then stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by combiflash (0 to 20% EtOAc/hexane) to provide 1.3 (0.4575 g, 90.78% yield). MS ESI (pos.) m/e: 382.0 (M+H2O)+. extracted with EtOAc The organic layers were washed with brine dried over Na2SO4 filtered concentrated purified by combiflash (0 to 20% EtOAc/hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 1.1 (2.0 g, 9.947 mmol) in DCM (50 mL) at 23° C. was added thionyl chloride (1.451 mL, 19.89 mmol) and allowed to stir overnight. The reaction was concentrated and then purified by combiflash (0 to 10% EtOAc/hexanes) to provide 1.2 (1.9940 g, 91.32% yield). The reaction was concentrated purified by combiflash (0 to 10% EtOAc/hexanes)