Triethylamine → 4,4,4-Trifluorobutyl methanesulfonate

HRID 1368187Notes

Reaction equation

HRID 1368187 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:6][CH2:5][CH2:4][CH2:3][C:2]([F:8])([F:7])[F:1])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1363074,4,4-Trifluorobutan-1-ol

Product 1

HCID 227256814,4,4-Trifluorobutyl methanesulfonateYield 988%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 4,4,4-trifluorobutanol (35 g; 0.027 mol) and triethylamine (28.3 g; 0.280 mol) in 200 ml of dichloromethane was treated dropwise at 0° C. with a solution of methanesulphonyl chloride (32.1 g; 0.280 mol) in 100 ml of dichloromethane. After the end of the addition, the mixture was stirred for a further 30 min, then poured onto ice and the phases were subsequently separated. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. 55 g of crude 4,4,4-trifluorobutyl methanesulphonate were obtained as an orange oil.

Workup

  1. additionAfter the end of the addition
  2. additionpoured onto ice
  3. customthe phases were subsequently separated
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e491c1d561146be8077018c72868b40
Source dataset
uspto-grants-2003_06
Patent number
US06573278B2

Reaction notes

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