Pyridine → 2,2,2-Trifluoroethyl Methanesulfonate

HRID 1056451Notes

Reaction equation

HRID 1056451 reaction equation
[C:1]([CH2:5][OH:6])([F:4])([F:3])[F:2].N1C=CC=CC=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15].Cl.N1C=CC=CC=1>>[C:1]([CH2:5][O:6][S:14]([CH3:13])(=[O:16])=[O:15])([F:4])([F:3])[F:2]

Participants

5

Reactant 4

HCID 1049PyridineHCID 64092,2,2-TrifluoroethanolHCID 31297Methanesulfonyl chlorideHCID 10176127Pyridinium chloride

Product 1

HCID 5565652,2,2-Trifluoroethyl Methanesulfonate

Procedure

A 10-L four-neck flask was equipped with a refluxing pipe and a dropping funnel to serve as a reactor. To the flask were added CF3CH2OH (337.1 g; 3.37 mol) and pyridine (306.31 g; 3.88 mol) in an ice bath, and the mixture was stirred. Using the dropping funnel, methanesulfonyl chloride (364.15 g; 3.20 mol) was dropped, with care for heat generation. The reaction solution changed its color gradually to milky white as pyridine hydrochloride was produced. After the end of the reaction, the reaction solution was washed with a 1 N HCl aqueous solution. The washed solution was separated to collect an organic layer.

Workup

  1. customA 10-L four-neck flask was equipped with a refluxing pipe and a dropping funnel
  2. customto serve as a reactor
  3. additionwas dropped, with care
  4. temperaturefor heat generation
  5. customwas produced
  6. customAfter the end of the reaction
  7. washthe reaction solution was washed with a 1 N HCl aqueous solution
  8. customThe washed solution was separated
  9. customto collect an organic layer

Sources & evidence

ORD record
ord-e0449065cd0742debd4aa4ce01398ae7
Source dataset
uspto-grants-2016_07
Patent number
US09397368B2

Reaction notes

Loading…