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1-Bromo-2-(chloromethyl)-4,5-dimethoxybenzene → 2-(2-Bromo-4,5-dimethoxy-benzyl)isoindole-1,3-dione

HRID 1186031
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HRID 1186031 반응식
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12]Cl.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][N:18]1[C:14](=[O:24])[C:15]2[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17]1=[O:19]
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참가 물질

5

반응물 2

HCID 49622811-Bromo-2-(chloromethyl)-4,5-dimethoxybenzeneHCID 24194345Phthalimide potassium salt

생성물 1

HCID 88657072-(2-Bromo-4,5-dimethoxy-benzyl)isoindole-1,3-dione

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A solution of 1-bromo-2-chloromethyl-4,5-dimethoxy-benzene (26.01 g, 0.09796 mol) in dry DMF (100 mL) was treated with potassium phthalimide (19.05 g, 0.1029 mol). The resulting slurry was heated to 80° C. while stirring under nitrogen for 4.5 h. The resulting mixture was then cooled to room temperature and allowed to stir 16 h. The resulting mixture solidified, was diluted with water (400 mL) and stirred 1 h. The resulting white precipitate was collected via filtration and washed with water (1 L). The white solid was dissolved in boiling methanol (2 L). The resulting solution was reduced to about 1 L, at which time a precipitate began to form. The resulting slurry was allowed to cool to room temperature then placed on an ice bath. The precipitate was collected via filtration to yield 2-(2-bromo-4,5-dimethoxy-benzyl)-isoindole-1,3-dione as a white solid.

후처리

  1. temperatureThe resulting mixture was then cooled to room temperature
  2. stirringto stir 16 h
  3. stirringstirred 1 h
  4. filtrationThe resulting white precipitate was collected via filtration
  5. washwashed with water (1 L)
  6. dissolutionThe white solid was dissolved
  7. customto form
  8. temperatureto cool to room temperature
  9. customthen placed on an ice bath
  10. filtrationThe precipitate was collected via filtration

출처 및 근거

ORD 기록
ord-bfff45a4ef294fe28467f0b43f6d481b
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08673890B2

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