Acetone → 4-Bromo-2-{[(3,5-dichlorophenyl)amino]methyl}phenol

HRID 2384318

반응식

HRID 2384318 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[N:5]=[CH:6][C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:8]=1[OH:14].[BH4-].[Na+].CC(C)=O.O>O1CCCC1.C(O)C>[Br:13][C:11]1[CH:10]=[CH:9][C:8]([OH:14])=[C:7]([CH2:6][NH:5][C:4]2[CH:15]=[C:16]([Cl:18])[CH:17]=[C:2]([Cl:1])[CH:3]=2)[CH:12]=1

참가 물질

7

반응물 4

HCID 180AcetoneHCID 962WaterHCID 7101644-Bromo-2-{[(3,5-dichlorophenyl)imino]methyl}phenolHCID 4311764Sodium borohydride

생성물 1

HCID 6772974-Bromo-2-{[(3,5-dichlorophenyl)amino]methyl}phenol수율 93.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

3,5-Dichloro-N-(5-bromo-2-hydroxybenzylidene)aniline (1.04 g, 3 mmol) was dissolved in tetrahydrofuran (12 mL) and ethanol (6 mL). Sodium borohydride (113 mg, 3 mmol) was added under ice cooling and argon atmosphere, and the mixture was stirred at room temperature for 12 hours. Acetone (10 mL) was added to the reaction mixture, and the residue obtained by concentration under reduced pressure was added water and extracted with dichloromethane. After the dichloromethane layer was washed with water and brine one after another, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give a light yellow viscous material. This was crystallized by n-hexane to give the title compound (971 mg, 93.3%) as a white crystal.

후처리

  1. customthe residue obtained by concentration under reduced pressure
  2. extractionextracted with dichloromethane
  3. washAfter the dichloromethane layer was washed with water and brine one after another,
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1)
  7. customto give a light yellow viscous material
  8. customThis was crystallized by n-hexane

출처 및 근거

ORD 기록
ord-d0a498dfd8eb442ca66071f178e88442
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263657B2

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