Potassium Phosphate, Tribasic → Methyl 5-[3-(methyloxy)propyl]-2-(methylthio)benzoate

Participants

Reaction Steps

To a THF (0.29 M) solution of 9-BBN (2 eq.) was added allyl methyl ether (2.1 eq.) dropwise and the resulting solution was stirred at RT until no more gaseous evolution was observed. The reaction mixture was then heated to 50° C. for 1 h. To this solution was subsequently added a DMF (0.34 M) solution of methyl 5-bromo-2-(methylthio)benzoate (1 eq.) from the previous step, potassium phosphate (2.5 eq.) and [1,1′-bis(diphenylphosphino)-ferrocene]dipalladium(II) dichloromethane complex (0.1 eq.). The resulting red suspension was heated at 80° C. for 16 h. After cooling to RT, the reaction was diluted with ether and water. The organic layer was separated and washed further with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→7:3 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Provenance & Evidence