1,1'-Carbonyldiimidazole → (5-Bromo-3-pyridinyl)methanol

Participants

Reaction Conditions

Reaction Steps

5-Bromonicotinic acid (3.44 g, 17.0 mmol) is placed in THF (40 mL), combined with CDI (3.00 g, 18.5 mmol) and stirred for 2 h at 50° C. Then while cooling with ice the reaction mixture is poured onto an aqueous NaBH4 solution (600 mg, 15.9 mmol in 100 mL H2O), stirred for 3 d at RT and extracted 7× with DCM. The combined organic phases are dried on Na2SO4, filtered and evaporated down using the rotary evaporator. The (5-bromo-pyridin-3-yl)-methanol thus obtained (HPLC-MS: tRet.=0.21 min; MS (M+H)+=188/190) is further used without any further purification steps.

Provenance & Evidence