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

HRID 46401

Reaction equation

HRID 46401 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-6a7202be207d4465aeb64585adedb843
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Linked notes

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