4-Toluenesulfonyl chloride → 2,2-Difluoroprop-1-yl toluene-4-sulphonate

HRID 222591Notes

Reaction equation

HRID 222591 reaction equation
[F:1][C:2]([F:6])([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>ClCCl>[F:1][C:2]([F:6])([CH3:5])[CH2:3][O:4][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 133948182,2-Difluoropropanol

Product 1

HCID 567765062,2-Difluoroprop-1-yl toluene-4-sulphonateYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2-difluoropropanol (0.50 g, 5.20 mmol) in dichloromethane (52.0 mL) and triethylamine (0.50 g, 0.73 mL, 5.20 mmol) at 0° C. is added p-toluenesulfonyl chloride (0.99 g, 5.20 mmol). The mixture is allowed to slowly warm to room temperature over 24 h. The mixture is concentrated and is partitioned between diethyl ether and water. The organic layer is washed with water and brine, dried over magnesium sulfate, filtered, and concentrated to dryness. The material is purified over silica gel to obtain 1.0 g of the title compound as clear crystals. MS (m/z) 250 (M+1).

Workup

  1. concentrationThe mixture is concentrated
  2. customis partitioned between diethyl ether and water
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe material is purified over silica gel

Sources & evidence

ORD record
ord-edbc2b3c4a1a4cb4a7af8d259f0756b6
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

Loading…