N,N-Diethylaniline → 1-(1-Chloroethyl)-3-(methylsulfonyl)benzene

HRID 415359Notes

Reaction equation

HRID 415359 reaction equation
S(Cl)([Cl:3])=O.C(N(CC)C1C=CC=CC=1)C.[CH3:16][S:17]([C:20]1[CH:21]=[C:22]([CH:26](O)[CH3:27])[CH:23]=[CH:24][CH:25]=1)(=[O:19])=[O:18].CCOC(C)=O>C1(C)C=CC=CC=1>[Cl:3][CH:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([S:17]([CH3:16])(=[O:19])=[O:18])[CH:21]=1)[CH3:27]

Participants

6

Reactant 4

HCID 7061N,N-DiethylanilineHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 666231181-(3-Methanesulfonylphenyl)ethan-1-ol

Product 1

HCID 666227631-(1-Chloroethyl)-3-(methylsulfonyl)benzeneYield 30.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (0.11 g, 0.91 mmol) was added to a solution of N,N-diethylaniline (0.19 g, 1.3 mmol) and 1-[3-(methylsulfonyl)phenyl]ethanol (0.26 g, 1.3 mmol) in toluene (4 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes followed by addition of EtOAc. The organic phase was washed subsequently with 2M HCl (aq), water, saturated sodium bicarbonate, and brine, and then dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash column chromatography on silica (ethyl acetate:hexane gradient elution 20:80 to 25:75) to give the title compound (60 mg) that was used in the next step without any further purification (approximate purity 75%).

Workup

  1. washThe organic phase was washed subsequently with 2M HCl (aq), water, saturated sodium bicarbonate, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography on silica (ethyl acetate:hexane gradient elution 20:80 to 25:75)

Sources & evidence

ORD record
ord-89333482e8d642b6802333120483c981
Source dataset
uspto-grants-2012_01
Patent number
US08088780B2

Reaction notes

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