Dimethylformamide → Tert-butyl 4'-(3-hydroxypropyl)biphenyl-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanol (37.9 mmol), tert-butyl 2-iodobenzoate (11.5 g, 37.9 mmol), sodium carbonate (10 g, 94.8 mmol), 1,1′-bis(diphenylphosphino)ferroncene-palladium dichloride dichloromethane complex (1:1), DMF (170 mL) and water (22 mL) was heated at 80° C. under nitrogen overnight. The reaction mixture was cooled to RT, poured into water, and the product was extracted with EtOAc-Hexanes (1:1). The combined organic extracts were washed with water and brine, dried (Na2SO4) and concentrated, and the residue was purified on silica gel (Hexane/EtOAc, from 2/1 to 1/1) to afford tert-butyl 4′-(3-hydroxypropyl)biphenyl-2-carboxylate.

Provenance & Evidence