Benzenesulfonyl chloride → HCID 689074, compound

HRID 432114Notes

Reaction equation

HRID 432114 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](=[O:19])[CH2:17]Br)=[CH:14][CH:13]=1>[Zn].O1CCCC1.O>[Br:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](=[O:19])[CH2:17][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 74544-Bromophenacyl bromide

Product 1

HCID 689074HCID 689074, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To benzenesulfonyl chloride (0.5 mL, 3.92 mmol) in 4:1 v/v tetrahydrofuran-water (20 mL) was added powdered zinc (282 mg, 4.31 mmol, 1.1 eq.) followed by 4-bromophenacyl bromide (1.31 g, 4.70 mmol, 1.2 eq.). The reaction mixture was stirred at room temperature for 17 hours. The volatile solvent was evaporated under reduced pressure and poured into water. The reaction was extracted with ethyl acetate (2×150 mL), and the combined organic layers were washed with brine (1×100 mL), dried (MgSO4), filtered, and evaporated under reduce pressure. The crude product was purified using MPLC (Biotage) eluted with 5:1 v/v hexane-ethyl acetate. Crystallization from dichloromethane-hexane gave the desired product as a white fluffy solid (486 mg, 36.6% yield). MS LC-MS (ES MH+=340); TLC (Rf=0.30, 25% ethyl acetate-hexane)

Workup

  1. customThe volatile solvent was evaporated under reduced pressure
  2. additionpoured into water
  3. extractionThe reaction was extracted with ethyl acetate (2×150 mL)
  4. washthe combined organic layers were washed with brine (1×100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified
  9. washeluted with 5:1 v/v hexane-ethyl acetate
  10. customCrystallization from dichloromethane-hexane

Sources & evidence

ORD record
ord-2686fe9e631f4f549d2dc828422a3cfc
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Reaction notes

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