4-Toluenesulfonyl chloride → HCID 118114175, compound

HRID 2178374Notes

Reaction equation

HRID 2178374 reaction equation
[F:1][C:2]([F:15])([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].C(N(CC)CC)C.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:2]([F:15])([F:1])[C:3]([F:5])([F:4])[F:6])=[CH:8][CH:9]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 75480873(4-(Pentafluoroethyl)phenyl)methanol

Product 1

HCID 118114175HCID 118114175, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-(perfluoroethyl)phenyl)methanol (0.60 g, 2.65 mmol) and triethylamine (0.53 g, 5.30 mmol) in dichloromethane (30 mL) was added p-toluenesulfonyl chloride (1.00 g, 5.30 mmol). The resulting mixture was allowed to stir at room temperature. After 2 h, the mixture was concentrated. Chromatographic purification of the residue (silica gel, 10% ethyl acetate in petroleum ether elute) afforded 0.400 g (40%) of 4-(perfluoroethyl)benzyl 4-methylbenzenesulfonate as a yellow oil.

Workup

  1. concentrationthe mixture was concentrated
  2. customChromatographic purification of the residue (silica gel, 10% ethyl acetate in petroleum ether elute)

Sources & evidence

ORD record
ord-9ed3e344b16e449085a7088b9acf4a88
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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