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

HRID 870336

Reaction equation

HRID 870336 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-782dc289896946e39552bcbe6e832e44
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Linked notes

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