Ethanone, 1-(3-bromo-5-nitrophenyl)- → HCID 87096355, compound

HRID 221709Notes

Reaction equation

HRID 221709 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11](=O)[CH3:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:14]([S@:18]([NH2:20])=[O:19])([CH3:17])([CH3:16])[CH3:15]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4](/[C:11](=[N:20]/[S:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:19])/[CH3:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 182852Ethanone, 1-(3-bromo-5-nitrophenyl)-HCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 87096355HCID 87096355, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Bromo-5-nitro-phenyl)-ethanone (11.6 g, 47.5 mmol), (R)-(+)-tert-butanesulfinamide (6.34 g, 52.3 mmol) and Ti(OEt)4 (24.64 ml, 119 mmol) were mixed in 62 ml THF and refluxed for 2.5 hrs. The reaction was cooled and carefully quenched by addition of ice and water. The white precipitate was filtered off and the aqueous mixture was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure. The crude product was purified by automated column chromatography (cyclohexane/ethyl acetate) yielding the title compound as yellow oil. 1H-NMR (500 MHz, DMSO-d6): 8.58 (s, 1H), 8.55 (s, 1H), 8.43 (s, 1H), 2.79 (s, 3H), 1.24 (s, 9H); MS: 347 [(M+H)+]; [α]D=+54.5° (c=0.481% in chloroform).

Workup

  1. temperaturerefluxed for 2.5 hrs
  2. temperatureThe reaction was cooled
  3. customcarefully quenched by addition of ice and water
  4. filtrationThe white precipitate was filtered off
  5. extractionthe aqueous mixture was extracted with ethyl acetate
  6. washThe organic phases were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. customVolatiles were removed under reduced pressure
  9. customThe crude product was purified by automated column chromatography (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-6b06be9ed6b448a1abd64007412887a2
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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