4-Bromotoluene → 2-Bromo-5-methylbenzene-1-sulfonyl chloride

HRID 842316Notes

Reaction equation

HRID 842316 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Cl:9][S:10](O)(=[O:12])=[O:11]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:10]([Cl:9])(=[O:12])=[O:11]

Participants

3

Reactant 2

HCID 78054-BromotolueneHCID 24638Chlorosulfonic acid

Product 1

HCID 151553382-Bromo-5-methylbenzene-1-sulfonyl chloride

Conditions

Temperature
0 °C

Procedure

40 g of 4-bromotoluene are slowly introduced into 250 ml of chlorosulfonic acid at −10° C. with stirring. The mixture is stirred at this temperature for 30 minutes, allowed to warm to 0° C. and poured onto excess ice. The product is filtered off with suction and washed with a little water. It is dried over P4O10 in vacuo and 63 g of a colorless solid are obtained, which is directly reacted further.

Workup

  1. stirringThe mixture is stirred at this temperature for 30 minutes
  2. additionpoured onto excess ice
  3. filtrationThe product is filtered off with suction
  4. washwashed with a little water
  5. dry with materialIt is dried over P4O10 in vacuo and 63 g of a colorless solid
  6. customare obtained
  7. customwhich is directly reacted further

Sources & evidence

ORD record
ord-f555d8e6a0ba461ab5a54dd633dfe57c
Source dataset
uspto-grants-2002_04
Patent number
US06372917B1

Reaction notes

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