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

HRID 888371ノート

反応式

HRID 888371 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-847f64dcfae7447094af1ac5560175c3
出典データセット
uspto-grants-2012_08
特許番号
US08247401B2

反応ノート

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