Bromomethyl 4-methoxyphenyl ketone → 2-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-isoindole-1,3(2H)-dione

HRID 751631노트

반응식

HRID 751631 반응식
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8]Br)=[CH:5][CH:4]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8][N:17]2[C:13](=[O:23])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16]2=[O:18])=[CH:5][CH:4]=1

참가 물질

4

반응물 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 24194345Phthalimide potassium salt

생성물 1

HCID 28156582-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-isoindole-1,3(2H)-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-methoxyphenacyl bromide (5.78 g, 25.23 mmol) in DMF (20 mL) was added potassium phthalimide (5.00 g, 26.99 mmol) and the reaction stirred at rt for 18 h. The reaction mixture was partitioned between dichloromethane (200 mL) and water (100 mL). The layers were separated and the aqueous layer extracted with dichloromethane (3×50 mL). The combined organics were washed with sodium hydroxide (2M, 50 mL), water (50 mL) and brine (50 mL) and dried (MgSO4). Filtration, then concentration in vacuo gave an off white solid. Trituration with diethyl ether followed by collection by filtration gave the title compound as a white solid. δH (CDCl3): 3.86 (3H, s), 5.15 (2H, s), 7.09 (2H, d), 7.81–8.01 (4H, m), 8.05 (2H, d).

후처리

  1. customThe reaction mixture was partitioned between dichloromethane (200 mL) and water (100 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane (3×50 mL)
  4. washThe combined organics were washed with sodium hydroxide (2M, 50 mL), water (50 mL) and brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration
  7. concentrationconcentration in vacuo
  8. customgave an off white solid
  9. filtrationTrituration with diethyl ether followed by collection by filtration

출처 및 근거

ORD 기록
ord-c54a7b75e66b4a26a0df7cf492f441b7
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405210B2

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