Chlorosulfonic acid → 1187082-98-9

HRID 2408367Notes

Reaction equation

HRID 2408367 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[Cl:12][S:13](O)(=[O:15])=[O:14]>>[Cl:12][S:13]([C:7]1[CH:6]=[C:5]([N+:8]([O-:10])=[O:9])[CH:4]=[C:3]([CH3:11])[C:2]=1[F:1])(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 575628801187082-98-9

Conditions

Temperature
110 °C

Procedure

A dry reaction flask equipped with a stirring bar, a reflux condenser and nitrogen inlet was charged with 4-fluoro-3-methylnitrobenzene (25) (3.10 g, 20 mmol). To this at 0° C., was added dropwise chlorosulfonic acid (5.29 mL, 80 mmol) over a period of 15 minutes. After bringing the homogeneous solution to room temperature, it was stirred at 110° C. for 24 hours. The resulting slurry was then poured over ice water (100 gm), extracted with diethyl ether (3×75 mL), and the organic phase washed with water (75 mL), then dried over anhydrous sodium sulfate. The solvent was then removed under reduced pressure to afford the corresponding sulfonyl chloride derivative (26), which was used further without purification.

Workup

  1. customA dry reaction flask
  2. customequipped with a stirring bar, a reflux condenser and nitrogen inlet
  3. customto room temperature
  4. extractionextracted with diethyl ether (3×75 mL)
  5. washthe organic phase washed with water (75 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-e9680b51203e4d74aa89d5fafd988602
Source dataset
uspto-grants-2014_08
Patent number
US08815848B2

Reaction notes

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