Diflunisal → 2',4'-Difluoro-4-hydroxy-5-iodo-1,1'-biphenyl-3-carboxylic acid

HRID 915611

反応式

HRID 915611 の反応式
FC(F)(F)C([O-])=O.[Tl+].FC(F)(F)C(O)=O.[CH:16]1[C:21]([C:22]2[CH:23]=[CH:24][C:25]([F:29])=[CH:26][C:27]=2[F:28])=[CH:20][C:19]([C:30]([OH:32])=[O:31])=[C:18]([OH:33])[CH:17]=1.[I-:34].[K+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>O>[F:28][C:27]1[CH:26]=[C:25]([F:29])[CH:24]=[CH:23][C:22]=1[C:21]1[CH:20]=[C:19]([C:30]([OH:32])=[O:31])[C:18]([OH:33])=[C:17]([I:34])[CH:16]=1

参加物

8

反応物 6

HCID 3059DiflunisalHCID 4875Potassium IodideHCID 6422Trifluoroacetic acid2 回HCID 14798Sodium HydroxideHCID 656671Sodium PyrosulfiteHCID 21902506Thallium(1+);2,2,2-trifluoroacetate2 回

生成物 1

HCID 43695632',4'-Difluoro-4-hydroxy-5-iodo-1,1'-biphenyl-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 20.6 g of thallium trifluoroacetate (TTFA, 31.9 mmol) and trifluoroacetic acid (TFA, 50 ml) was stirred in a flask until the TTFA dissolved. This solution was added at room temperature to a flask containing 51 g (205 mmol) of diflunisal and it was stirred for 30 min. A solution of potassium iodide (KI, 40.9 g, 245.6 mmol) in 120 ml of water was slowly added to the mixture. After the reaction finished, the product was worked up. First, sodium metabisulphite (NaS2O5, 5.01 g, 26.4 mmol) was added to reduce the species of TI (III) to TI (I), and then a solution of sodium hydroxide was added to neutralize the TFA. It was extracted with dichloromethane and the organic phase was washed with water and dried over magnesium sulphate. The solvent was evaporated at low pressure and a crude was obtained of 96% purity, which was purified by chromatography on a silica gel column using the appropriate eluents.

後処理

  1. dissolutiondissolved
  2. additionThis solution was added at room temperature to a flask
  3. extractionIt was extracted with dichloromethane
  4. washthe organic phase was washed with water
  5. dry with materialdried over magnesium sulphate
  6. customThe solvent was evaporated at low pressure
  7. customa crude was obtained of 96% purity, which
  8. customwas purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-10b9ed656e3b40069c8a6f6652458f9c
出典データセット
uspto-grants-2007_09
特許番号
US07265245B2

関連ノート

読み込み中…