Chloroform → 2,4-Difluoro-5-methylbenzenesulfonyl chloride

HRID 1402071

Reaction equation

HRID 1402071 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[CH3:14].C(Cl)(Cl)Cl>>[F:13][C:11]1[CH:12]=[C:7]([F:6])[C:8]([CH3:14])=[CH:9][C:10]=1[S:2]([Cl:1])(=[O:5])=[O:3]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 24638Chlorosulfonic acid2×HCID 679832,4-Difluoro-1-methylbenzene

Product 1

HCID 594365302,4-Difluoro-5-methylbenzenesulfonyl chlorideYield 75.1%

Procedure

Chlorosulfonic acid (5.2 mL, 0.078 mol) was added dropwise to a solution of 2,4-difluorotoluene (4.00 g, 0.0312 mol) in chloroform (75 mL, 0.94 mol). The reaction was stirred 2 hours. Additional chlorosulfonic acid (3.1 mL, 0.047 mol) was added and stirring was continued for 18 hours. The reaction was evaporated to an oil and poured onto ice. The mixture was extracted two times with ethyl ether. The combined organic phase was dried over magnesium sulfate and treated with activated carbon. The mixture was filtered through diatomaceous earth and the filtrate was evaporated to give 5.31 g of light brown oil.

Workup

  1. stirringstirring
  2. waitwas continued for 18 hours
  3. customThe reaction was evaporated to an oil
  4. additionpoured onto ice
  5. extractionThe mixture was extracted two times with ethyl ether
  6. dry with materialThe combined organic phase was dried over magnesium sulfate
  7. additiontreated with activated carbon
  8. filtrationThe mixture was filtered through diatomaceous earth
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c566f74ba0cc4c9e9fa41db9f2e572a0
Source dataset
uspto-grants-2014_12
Patent number
US08907101B2

Linked notes

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