Water → Benzenemethanol,2-fluoro-,1-methansulfonate

HRID 450868Notes

Reaction equation

HRID 450868 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>ClCCl>[CH3:17][S:18]([O:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[F:1])(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 679692-Fluorobenzylic alcohol

Product 1

HCID 21964506Benzenemethanol,2-fluoro-,1-methansulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-Fluorobenzyl alcohol (10 g, 79.28 mmol) in dry dichloromethane (200 ml) was added triethylamine (12.03 g, 118.9 mmol) under argon at room temperature. Methanesulfonyl chloride (10.71 g, 93.5 mmol) was added to the above reaction mixture at 0° C., and stirring was continued for another 3 hours. Water (100 ml) was added to the reaction mixture and the mixture was extracted twice with dichloromethane. The combined organic layers were washed with water and brine. The reaction mixture was dried over Na2SO4, filtered and concentrated to give the title compound as an yellow oil which was used without further purification.

Workup

  1. extractionthe mixture was extracted twice with dichloromethane
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialThe reaction mixture was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-780a8c2f86eb40b9a06edf01436bced6
Source dataset
uspto-grants-2013_07
Patent number
US08487000B2

Reaction notes

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