Methanesulfonyl chloride → 4,4,4-Trifluorobutyl methanesulfonate

HRID 2200602Notes

Reaction equation

HRID 2200602 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][CH2:4][CH2:5][OH:6].[CH3:9][S:10](Cl)(=[O:12])=[O:11]>C(Cl)Cl>[CH3:9][S:10]([O:6][CH2:5][CH2:4][CH2:3][C:2]([F:8])([F:7])[F:1])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1363074,4,4-Trifluorobutan-1-ol

Product 1

HCID 227256814,4,4-Trifluorobutyl methanesulfonateYield 31.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,4,4-trifluorobutan-1-ol (100 mg, 83 mmol) in dry DCM (2 mL) was added methanesulfonyl chloride (107.3 mg, 72 mmol) and then by TEA (158 mg, 216 mmol) at 0° C. The reaction was stirred at room temperature for 1 h. The reaction was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give a yellow oil product (50 mg, 31.1% yield), which was used without purification. Product tlc [petroleum ether/ethyl acetate (3:1) Rf 0.4]

Workup

  1. customat 0° C
  2. customThe reaction was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-749dbf3e95b343f7ae9302f85ec53cbd
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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