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

HRID 2196821Notes

Reaction equation

HRID 2196821 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>C(Cl)Cl>[CH3:17][S:18]([O:9][CH2:8][C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 147614612-Fluoro-3-(hydroxymethyl)pyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-fluoropyridin-3-yl)methanol (200 mg, 1.57 mmol) and triethylamine (658 μL, 4.72 mmol) in CH2Cl2 (10 mL) was added methanesulfonyl chloride (269 mg, 2.36 mmol). The reaction mixture was kept at 0° C. for 30 min., poured into water, and the mixture was extracted with CH2Cl2 (2×20 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The product was used without further purification.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (2×20 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe product was used without further purification

Sources & evidence

ORD record
ord-4e5e8977152d43c0bd6cf82aef445983
Source dataset
uspto-grants-2012_12
Patent number
US08338467B2

Reaction notes

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