4-Toluenesulfonyl chloride → HCID 19882835, compound

HRID 846503Notes

Reaction equation

HRID 846503 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[Cl:1])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 748142-Chloro-4-fluorophenol

Product 1

HCID 19882835HCID 19882835, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred solution of 20.0 g (0.137 mole) of 2-chloro-4-fluorophenol in 150 mL of pyridine was cooled in an ice bath. To this solution was added portionwise 31.2 g (0.164 mole) of 4-methylphenylsulfonyl chloride. After complete addition, the mixture was stirred for 2 hours, then allowed to stand in a freezer for approximately 16 hours. The mixture was poured into ice water, filtered, and the filter cake washed with water. The solid was dried in a dessicator to yield 41.0 g of 2-chloro-4-fluorophenyl 4-methylphenylsulfonate, mp 92°-94° C.

Workup

  1. additionAfter complete addition
  2. waitto stand in a freezer for approximately 16 hours
  3. filtrationfiltered
  4. washthe filter cake washed with water
  5. customThe solid was dried in a dessicator

Sources & evidence

ORD record
ord-dbec6042081941d6a8d615bbfeec7236
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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