Boron tribromide → HCID 21079763, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4h (3.38 g; 14.30 mmol) and CH2Cl2 (150 mL) were cooled to −78° C. and a solution of BBr3 (5.41 mL; 57.22 mmol) in 130 mL of CH2Cl2 were added dropwise over a 30 m period. The reaction mixture was stirred at −78° C. for 1 h, allowed to warm to rt for 4 h and re-cooled to −78° C. and carefully quenched with sat'd. NaHCO3 (80 mL). The aqueous layer was extracted with CH2Cl2 (1×100 mL), EtOAc (50 mL) and the combined aqueous layers washed with water and brine, dried (Na2SO4) and evaporated to yield a light brown oil. The phenol was purified by silica gel chromatography and eluted with CH2Cl2:hexane (3:1)→CH2Cl2→CH2Cl2:EtOAc (100:4) to yield ethyl 4-iso-propyl-3-hydroxyphenylacetate (5c; 3.0 g; 94%)

Provenance & Evidence