Chlorosulfonic acid → 4-((S)-2-Fluoro-1-methyl-ethyl)-benzenesulfonyl chloride

HRID 2357002Notes

Reaction equation

HRID 2357002 reaction equation
[F:1][CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:4].[Cl:11][S:12](O)(=[O:14])=[O:13]>ClCCl>[F:1][CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][C:8]([S:12]([Cl:11])(=[O:14])=[O:13])=[CH:7][CH:6]=1)[CH3:4]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 53628601((S)-2-Fluoro-1-methyl-ethyl)-benzene

Product 1

HCID 536286004-((S)-2-Fluoro-1-methyl-ethyl)-benzenesulfonyl chlorideYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
30 °C

Procedure

3.5 g of ((S)-2-fluoro-1-methyl-ethyl)-benzene (25.32 mmol) were dissolved in 80 ml of dichloromethane. At 0-5° C., 11.81 g of chlorosulfonic acid (101.31 mmol), dissolved in 20 ml of dichloromethane, were added dropwise. The reaction mixture was stirred for 30 min at room temperature and 2 h at 30° C. The solvent was evaporated. 150 ml of diethyl ether were added to the residue, washed once with 150 ml water, and the organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified via silica gel chromatography with n-heptane-dichloromethane (6:4) as eluent to give 1.5 g of the title compound.

Workup

  1. additionwere added dropwise
  2. customThe solvent was evaporated
  3. addition150 ml of diethyl ether were added to the residue
  4. washwashed once with 150 ml water
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customThe crude product was purified via silica gel chromatography with n-heptane-dichloromethane (6:4) as eluent

Sources & evidence

ORD record
ord-4a1cb66298f842faa42ef5d7a94e6f8c
Source dataset
uspto-grants-2010_07
Patent number
US07759397B2

Reaction notes

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