2,6-Lutidine → 2-bromoethyl trifluoromethanesulfonate

HRID 1634915Notes

Reaction equation

HRID 1634915 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Br:16][CH:17](O)[CH3:18].N1C(C)=CC=CC=1C>C(Cl)Cl>[Br:16][CH2:17][CH2:18][O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 14202443Ethanol, 1-bromo-

Product 1

HCID 109231692-bromoethyl trifluoromethanesulfonateYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

240 g of trifluoromethanesulfonic anhydride (0.85 mol) are added in 1.5 h, under inert atmosphere, to a solution of bromoethanol (57 mL; 0.80 mol) and 2,6-lutidine (104 mL; 0.89 mol) in CH2Cl2 cooled at −5° C. After 10 min the mixture is concentrated to one fourth the volume, then eluted through a small layer of silica gel (eluent n-hexane/EtOAc=9:1). By evaporation and drying, the desired product is obtained (147.2 g; 0.57 mol).

Workup

  1. concentrationAfter 10 min the mixture is concentrated to one fourth the volume
  2. washeluted through a small layer of silica gel (eluent n-hexane/EtOAc=9:1)
  3. customBy evaporation
  4. customdrying

Sources & evidence

ORD record
ord-ed9987266a794b7ca1c3fe47efb5880e
Source dataset
uspto-grants-2003_01
Patent number
US06509324B1

Reaction notes

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