2,6-Lutidine → 2-Fluoro-2-methylpropyl trifluoromethanesulfonate

HRID 20423Notes

Reaction equation

HRID 20423 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[F:16][C:17]([CH3:21])([CH3:20])[CH2:18]O.N1C(C)=CC=CC=1C>ClCCl>[F:16][C:17]([CH3:21])([CH3:20])[CH2:18][O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 111261792-Fluoro-2-methylpropan-1-ol

Product 1

HCID 121655342-Fluoro-2-methylpropyl trifluoromethanesulfonateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoromethanesulphonic anhydride (4.3 mL, 26.0 mmol) to a solution of 2-fluoro-2-methylpropan-1-ol (2.0 g, 21.7 mmol) and 2,6-lutidine (3.0 mL, 26.0 mmol) in dichloromethane (25 mL) at −78° C. Warm slowly to room temperature and stir at room temperature for 1 hour. Add water to quench the reaction, separate the organic layer and extract the aqueous layer with dichloromethane. Combine the organic layers, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with dichloromethane), to give the desired compound as an oil (3.4 g, 70% yield).

Workup

  1. customAdd water to quench
  2. customthe reaction
  3. customseparate the organic layer
  4. extractionextract the aqueous layer with dichloromethane
  5. dry with materialdry (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with dichloromethane)

Sources & evidence

ORD record
ord-e194009f2c234d79af1e5d5eb84cacb0
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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