Triethylamine → (2-Fluoropyridin-3-yl)methyl methanesulfonate

HRID 594968Notes

Reaction equation

HRID 594968 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:10][S:11](Cl)(=[O:13])=[O:12].C(N(CC)CC)C>ClCCl>[CH3:10][S:11]([O:9][CH2:8][C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 147614612-Fluoro-3-(hydroxymethyl)pyridine

Product 1

HCID 86634652(2-Fluoropyridin-3-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (2-fluoropyridin-3-yl)methanol (400 mg, 3.1 mmol), methanesulfonyl chloride (0.37 mL, 4.7 mmol) and triethylamine (0.88 mL, 6.30 mmol) in dichloromethane (10 mL) was stirred at rt for 16 h. The mixture was then diluted with dichloromethane and washed with H2O, then brine. The organic phase was collected, dried (MgSO4) and concentrated in vacuo to give (2-fluoropyridin-3-yl)methyl methanesulfonate.

Workup

  1. washwashed with H2O
  2. customThe organic phase was collected
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fb0a970e0324ed3a251cb256e4adeca
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

Loading…