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

HRID 1517564Notes

Reaction equation

HRID 1517564 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

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14761460(2-Bromopyridin-3-yl)methanol

Product 1

HCID 58268552(2-Bromo-3-pyridyl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. washAfter that time the mixture is washed with water and organic layer
  2. customis decanted
  3. dry with materialdried over magnesium sulfate and solvent
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-593bcd02dce941f9b453c909b64faf74
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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