Triethylamine → 2-Fluoroethyl p-Toluenesulfonate

HRID 2200151Notes

Reaction equation

HRID 2200151 reaction equation
[C:1]1(C)[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[F:12][CH2:13][CH2:14][OH:15].[CH2:16](N(CC)CC)C>ClCCl>[CH3:16][C:5]1[CH:6]=[CH:1][C:2]([S:7]([O:15][CH2:14][CH2:13][F:12])(=[O:8])=[O:9])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 97372-Fluoroethanol

Product 1

HCID 2560192-Fluoroethyl p-ToluenesulfonateYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add toluenesulfonyl chloride (1.8 g, 9.4 mmol) to the mixture of 2-fluoroethanol (500 mg, 7.8 mmol) and triethylamine (1.6 g, 15.6 mmol) in dichloromethane (30 mL) at 0-5° C. Stir the reaction at ambient temperature for 5 hrs. Remove the volatiles under reduced pressure to yield the crude product. Purify by flash chromatography (silica gel, PE:EtOAc=2:1) to afford a white solid as the title compound (1.3 g, 77%).

Workup

  1. customthe reaction at ambient temperature for 5 hrs
  2. customRemove the volatiles under reduced pressure
  3. customto yield the crude product
  4. customPurify by flash chromatography (silica gel, PE:EtOAc=2:1)

Sources & evidence

ORD record
ord-d670e295fef04502bbabf602e0c280c1
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

Loading…