Sodium Thiosulfate → tert-Butyl 3-bromo-5-(trifluoroacetyl)benzoate

HRID 888371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 888371
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:25]=[C:26]([CH:34]=[C:35]([CH:37]([OH:42])[C:38]([F:41])([F:40])[F:39])[CH:36]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:23][C:24]1[CH:25]=[C:26]([CH:34]=[C:35]([C:37](=[O:42])[C:38]([F:40])([F:41])[F:39])[CH:36]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28]

Komponenten

6

Edukt 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59539580Tert-butyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate

Produkt 1

HCID 68496903tert-Butyl 3-bromo-5-(trifluoroacetyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dess-Martin reagant (7.8 g, 18.6 mmol) was added to a solution of tert-Butyl 3-bromo-5-[(R/S)-2,2,2-trifluoro-1-hydroxyethyl]benzoate (4.4 g, 12.4 mmol) in DCM (75 mL). The reaction was stirred for one hour and saturated aq. Na2S2O3 and aq. NaHCO3 were added. The reaction was extracted with DCM (3×) and the organic layers combined and washed with brine, dried over Na2SO4 and concentrated to dryness. Purification using automated flash chromatography (SiO2, 120 g, 0-10% MeOH(NH4OH)/DCM) gave final compound as a mixture of hydrate and ketone which was used directly in step B.

Aufarbeitung

  1. extractionThe reaction was extracted with DCM (3×)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-847f64dcfae7447094af1ac5560175c3
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247401B2

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