Water → 1-[2-(p-Toluenesulfonyloxy)ethyl]-2,3,6-trifluorobenzene

HRID 1722298Notes

Reaction equation

HRID 1722298 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][CH2:11][OH:12].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C.O>C(Cl)Cl>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:12][CH2:11][CH2:10][C:3]2[C:4]([F:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 148346752-(2,3,6-Trifluorophenyl)ethan-1-ol

Product 1

HCID 156318391-[2-(p-Toluenesulfonyloxy)ethyl]-2,3,6-trifluorobenzeneYield 120.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,3,6-trifluorophenyl)ethyl alcohol (1.5 g) in methylene chloride (10 ml) are added with stirring p-toluenesulfonyl chloride (2.2 g) and triethylamine (2.0 ml), and the mixture is stirred at room temperature for 5 hours. The reaction mixture is poured into water and is extracted with diethyl ether. The ether layer is washed with aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride and dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (solvent, methylene chloride) and recrystallized from diethyl ether-n-hexane to give 1-[2-(p-toluenesulfonyloxy)ethyl]-2,3,6-trifluorobenzene (3.4 g), as colorless prisms, m.p. 73°-74° C.

Workup

  1. extractionis extracted with diethyl ether
  2. washThe ether layer is washed with aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (solvent, methylene chloride)
  6. customrecrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-56802875b3ef47dd90d8a805c77058fe
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

Loading…