Water → 4,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonate

HRID 515802Notes

Reaction equation

HRID 515802 reaction equation
[F:1][C:2]([F:11])([C:7]([F:10])([F:9])[F:8])[CH2:3][CH2:4][CH2:5][OH:6].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O:6][CH2:5][CH2:4][CH2:3][C:2]([F:11])([F:1])[C:7]([F:8])([F:9])[F:10])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 5479674,4,5,5,5-Pentafluoropentan-1-ol

Product 1

HCID 220330274,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonateYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,4,5,5,5-pentafluoropentan-1-ol (1 g, 5.6 mmol), p-toluenesulfonylchloride (1.3 g, 6.8 mmol), and triethylamine (1.2 mL, 8.4 mmol) in DCM (20 mL) was stirred at room temperature for 18 h. Water was added to the reaction mixture, the two layers were separated, and the aqueous layer was extracted with DCM (2×). The organics were combined, dried over sodium sulfate, and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 0 to 20% EtOAc/hexanes to afford 1.7 g of 4,4,5,5,5-pentafluoropentyl 4-methylbenzenesulfonate as a colorless oil.

Workup

  1. customthe two layers were separated
  2. extractionthe aqueous layer was extracted with DCM (2×)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel eluting with 0 to 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-45186e51e05b47b7a00aa3bd76654222
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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