2-Chloroethanol → 2-Chloroethyl trifluoromethanesulfonate

HRID 2108366

Reaction equation

HRID 2108366 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[Cl:16][CH2:17][CH2:18]O.N1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:5][C:4]([F:7])([F:6])[S:1]([O:8][CH2:18][CH2:17][Cl:16])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 1005252-Chloroethyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of triflic anhydride (2.0 mL, 11.9 mmol) in CCl4 (10 mL) at 0° C. was treated with a solution of 2-chloroethanol (0.8 mL, 11.9 mmol) and pyridine (0.96 mL, 11.9 mmol) in CCl4 (6.0 mL) which was pre-cooled to 0° C. The reaction mixture was stirred at 0° C. for 45 minutes and then filtered through a pad of Na2SO4. The filtrate was concentrated and used immediately in the next step.

Workup

  1. filtrationfiltered through a pad of Na2SO4
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-34b7e7b7c1094e9f844c0b8f5b74f1fb
Source dataset
uspto-grants-2009_04
Patent number
US07514435B2

Linked notes

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