Methanesulfonyl chloride → (2-Fluoropyridin-4-yl)methyl methanesulfonate

HRID 61884Notes

Reaction equation

HRID 61884 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[S:10](Cl)([CH3:13])(=[O:12])=[O:11]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11332468(2-Fluoropyridin-4-yl)methanol

Product 1

HCID 10488448(2-Fluoropyridin-4-yl)methyl methanesulfonateYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2-Fluoropyridin-4-yl) methanol (1 g) was dissolved in DCM (40 ml), added with TEA (3.3 ml) and mesyl chloride (0.67 ml), and the mixture was stirred at 0° C. for 1 hr. The mixture was concentrated and then purified by silica gel column (n-hexane/ethyl acetate=4/1) to obtain the title compound (1.18 g, 77%).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel column (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-d32690f3365648ecbf48da9b44defd66
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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