Benzene, 1-bromo-3-ethyl- → (4-bromo-1-trityl-1H-imidazol-2-yl)(3-ethylphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-3-ethylbenzene (266 mg, 1.44 mmol) in 7 mL THF at −78° C., was added BuLi (1.6 M in hexanes, 0.99 mL, 1.58 mmol). The mixture was stirred at −78° C. for 10 min, then a solution of Intermediate 175.1 (600 mg, 1.44 mmol) in 3 mL THF was added. The mixture was stirred at −78° C. for 1 h, then was removed from the cooling bath and stirred 20 min. The reaction was quenched with sat. NH4Cl, then was diluted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient) to afford 585 mg of Intermediate 175.2 as a colorless solid. LCMS (4 min gradient, 50 to 100% B, A=95% H2O/5% CH3CN/0.1% TFA, B=95% CH3CN/5% H2O/0.1% TFA) RT=3.65 min, 523.10 (M+H)+.

Provenance & Evidence