Water → 1-Bromo-2-(propane-2-sulfonyl)benzene

HRID 1438116Notes

Reaction equation

HRID 1438116 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH:9]([CH3:11])[CH3:10].[OH:12]OS([O-])=O.[K+].[OH2:18]>CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH:9]([CH3:11])[CH3:10])(=[O:12])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 57942784HCID 57942784, compound

Product 1

HCID 229536121-Bromo-2-(propane-2-sulfonyl)benzeneYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 21A (0.7 g, 3.0 mmol) in methanol (5 mL) was added oxone®8 (5.6 g, 9.0 mmol) in water (5 mL). The reaction was stirred at rt for 4 h. The reaction was quenched with 5% NaHSO3 and then neutralized with 1 M NaOH. The organic solvent was evaporated and the aqueous layer was extracted with dichloromethane (3×). The combined extracts were washed with brine and dried over sodium sulfate. The solvent was removed to give 0.53 g of product 21B (67% yield). 1H NMR (400 MHz, Methanol-d4) δ ppm 1.26 (d, J=6.85 Hz, 6H) 3.80-4.00 (m, 1H) 7.45-7.68 (m, 2H) 7.87 (dd, J=7.46, 1.59 Hz, 1H) 8.10 (dd, J=7.34, 2.20 Hz, 1H).

Workup

  1. customThe reaction was quenched with 5% NaHSO3
  2. customThe organic solvent was evaporated
  3. extractionthe aqueous layer was extracted with dichloromethane (3×)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-f30811f20f834cb98bf3a0521b555ef6
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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