4-Chlorophenyl phenyl ether → 4-(4-Chlorophenoxy)benzene-1-sulfonyl chloride

HRID 380583Notes

Reaction equation

HRID 380583 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=1>>[Cl:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 234364-Chlorophenyl phenyl etherHCID 24638Chlorosulfonic acid

Product 1

HCID 27577504-(4-Chlorophenoxy)benzene-1-sulfonyl chloride

Procedure

Chlorosulfonic acid (9.7 mL, 0.147 mole) was added dropwise to 4-chlorophenoxybenzene (12.6 mL, 73.4 mmole) at room temperature with stirring. When addition was complete, the mixture was stirred at room temperature for 1 hour and then poured into ice water. The solid was collected by filtration, dried in the air, and recrystallized from petroleum ether and ethyl acetate to give 4-(4-chlorophenoxy)benzenesulfonylohloride (7.43 grams, 33%).

Workup

  1. additionWhen addition
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. filtrationThe solid was collected by filtration
  4. customdried in the air
  5. customrecrystallized from petroleum ether and ethyl acetate
  6. customto give 4-(4-chlorophenoxy)benzenesulfonylohloride (7.43 grams, 33%)

Sources & evidence

ORD record
ord-aa87332888c841f8aea58228c5854bed
Source dataset
uspto-grants-2001_10
Patent number
US06303636B1

Reaction notes

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