Water → HCID 26948597, compound

HRID 434014Notes

Reaction equation

HRID 434014 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].CCN(CC)CC.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:25])=[O:24])=[CH:4][C:3]=1[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 17324-Chloro-3-methylphenolHCID 7369Benzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 26948597HCID 26948597, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-chloro-3-methylphenol (1.0 g, 7.0 mmol) in dry CH2Cl2 (70 mL) at 0° C. was added Et3N (1.45 mL, 10.5 mmol). After stirring at 0° C. for 20 min, benzenesulfonyl chloride (1.34 mL, 10.5 mmol) was added to the reaction mixture. The reaction was slowly warmed to room temperature and stirring was continued for an additional 18 h. Water was added to quench the reaction and the organic layer was washed with brine and dried over Na2SO4. The solvent was removed in vacuo and resulting crude product was purified by flash column chromatography (silica gel, 10-30% CH2Cl2/hexanes). The desired product was obtained as a white solid (1.9 g, 96%). LC/MS (ES+) m/e 283.0 [M+H]+.

Workup

  1. temperatureThe reaction was slowly warmed to room temperature
  2. stirringstirring
  3. waitwas continued for an additional 18 h
  4. customto quench
  5. customthe reaction
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed in vacuo
  9. customresulting crude product
  10. customwas purified by flash column chromatography (silica gel, 10-30% CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-733a5aaa721646a389e96d24a5cab0d4
Source dataset
uspto-grants-2003_12
Patent number
US06670388B1

Reaction notes

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