Chlorosulfonic acid → 4-(4-Chlorosulfonylbenzyl)-nitrobenzene

HRID 634810Notes

Reaction equation

HRID 634810 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17][S:18](O)(=[O:20])=[O:19]>ClCCl>[Cl:17][S:18]([C:5]1[CH:4]=[CH:3][C:2]([CH2:1][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:7][CH:6]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1372254-Nitrodiphenylmethane

Product 1

HCID 218768654-(4-Chlorosulfonylbenzyl)-nitrobenzeneYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-benzyl-nitrobenzene (4.26 g, 70 mmol) dissolved in dichloromethane (25 mL) was added dropwise to a solution of chlorosulfonic acid (6 mL) in dichloromethane (25 mL) at−30° C. The mixture was stirred for 10 minutes at 0° C., then poured onto ice and shaken. The organic phase was separated and solvents were evaporated. The residue was recrystallized from dichloromethane/hexanes to yield 4-(4-chlorosulfonylbenzyl)-nitrobenzene (5.52 g, 78%) as dichloromethane hemisolvate crystals.

Workup

  1. additionpoured onto ice
  2. stirringshaken
  3. customThe organic phase was separated
  4. customsolvents were evaporated
  5. customThe residue was recrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-4525d87e869d40c0bad95eddb5cd2957
Source dataset
uspto-grants-2001_02
Patent number
US06184242B2

Reaction notes

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