Triethylamine → (2-Bromo-3-pyridyl)methyl methanesulfonate

Reaction equation

C(N(CC)CC)C.[Br:8][C:9]1[C:14]([CH2:15][OH:16])=[CH:13][CH:12]=[CH:11][N:10]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:16][CH2:15][C:14]1[C:9]([Br:8])=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:20])=[O:19]

Participants

Procedure

Triethylamine (8.90 mL) is added to a round bottom flask containing a solution of (2-bromopyridin-3-yl)methanol (8 g, 42.55 mmol) in dichloromethane (212 mL) at 0° C., then methanesulfonyl chloride (3.95 mL) is added and the mixture is stirred at that temperature for 1.5 h. After that time the mixture is washed with water and organic layer is decanted, dried over magnesium sulfate and solvent evaporated under reduced pressure to yield 10.4 g of the title compound used without further purification. MS (m/z): 266, 268 (M+1; M+3).