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

HRID 888371노트

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HRID 888371 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-847f64dcfae7447094af1ac5560175c3
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247401B2

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