2,3-Dichloroanisole → 2,3-Dichloro-4-methoxybenzene-1-sulfonyl chloride

HRID 485880Notes

Reaction equation

HRID 485880 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Cl:11][S:12](O)(=[O:14])=[O:13]>>[Cl:8][C:7]1[C:2]([Cl:1])=[C:3]([O:9][CH3:10])[CH:4]=[CH:5][C:6]=1[S:12]([Cl:11])(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 161262,3-DichloroanisoleHCID 24638Chlorosulfonic acid

Product 1

HCID 159142682,3-Dichloro-4-methoxybenzene-1-sulfonyl chloride

Procedure

To 5.31 g of 2,3-dichloroanisole is slowly added 10 ml of chlorosulfonic acid over a period of 30 minutes. The reaction is mildly exothermic and at the end of the addition, a clear solution is formed. The yellowish solution is stirred at room temperature for 1 additional hour and quenched with 200 g of crushed ice. The solid is filtered, air-dried and recrystallized from ether-pentane to give 6.9 g of 2,3-dichloro-4-methoxybenzenesulfonyl chloride as off-white prisms, mp 93°-95°.

Workup

  1. customof 30 minutes
  2. additionThe reaction is mildly exothermic and at the end of the addition
  3. customa clear solution is formed
  4. customquenched with 200 g of crushed ice
  5. filtrationThe solid is filtered
  6. customair-dried
  7. customrecrystallized from ether-pentane

Sources & evidence

ORD record
ord-132c705df3354c0d810d8552b01cae1d
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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