Iodine → 4-Chloro-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21007

반응식

HRID 21007 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([OH:21])[N:5]([C:12]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])[C:6]2=[O:11].CN(CCN(C)C)C.C([Li])(CC)C.CCCCCC.[I:41]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:41])=[C:7]2[C:3]=1[CH:4]([OH:21])[N:5]([C:12]([CH3:13])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:20])[C:6]2=[O:11]

참가 물질

7

반응물 5

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 24477Sodium ThiosulfateHCID 684900434-Chloro-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinoneHCID 178444656HCID 178444656, 화합물

생성물 1

HCID 684876174-Chloro-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Chloro-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (6.86 g, 22.7 mmol) was dissolved in THF (274 mL), and the solution was added with TMEDA (7.55 mL, 50.0 mmol), then added with sec-butyllithium-hexane solution (0.99 mol/L, 50.5 mL, 50.0 mmol) by drops at −78° C. over 20 minutes under argon atmosphere, followed by stirring at the same temperature for 2 hours. Then, the mixture was added with iodine (6.92 g, 27.3 mmol) and warmed from −78° C. to room temperature for 2.5 hours. The reaction mixture was added with 10% aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol=100/0, 85/15) to obtain 4-chloro-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (8.22 g, yield 85%).

후처리

  1. temperaturewarmed from −78° C. to room temperature for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by flash column chromatography (chloroform/methanol=100/0, 85/15)

출처 및 근거

ORD 기록
ord-38562bcbda7b46d98c2c165e454b3966
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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