Azobisisobutyronitrile → 2-(4-Bromomethyl-thiophen-3-ylmethyl)-isoindole-1,3-dione

HRID 251251노트

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HRID 251251 반응식
[CH3:1][CH:2]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].C1C(=O)N([Br:26])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:1][C:2]1[C:3]([CH2:7][N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[CH:4][S:5][CH:6]=1

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 672731652-(4-Methyl-tetrahydro-thiophen-3-ylmethyl)-isoindole-1,3-dione

생성물 1

HCID 672716532-(4-Bromomethyl-thiophen-3-ylmethyl)-isoindole-1,3-dione수율 53.3%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

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온도
85 °C

실험 절차

2-(4-Methyl-tetrahydro-thiophen-3-ylmethyl)-isoindole-1,3-dione (410.0 mg, 1.59 mmol) and NBS (312.0 mg, 1.75 mmol) were dissolved in CCl4 (8.0 mL). AIBN (100 mg) was added in one portion. The mixture was heated at 85° C. under N2 for 90 min. After cooling down, the mixture was passed through a short silica gel column (4×10 cm), eluted with CH2Cl2. The solution obtained was concentrated and the residue was recrystallized from EtOAc/Hexanes (5/1) to give 2-(4-Bromomethyl-thiophen-3-ylmethyl)-isoindole-1,3-dione (285 mg, 50%) as a white solid. 1H NMR (CDCl3) δ 4.74 (s, 2H), 4.91 (s, 2H), 7.29-7.30 (d, 1H, J=3.3 Hz), 7.70-7.71 (d, 1H, J=3.3 Hz), 7.70-7.73 (m, 2H), 7.82-7.87 (m, 2H).

후처리

  1. temperatureAfter cooling down
  2. washeluted with CH2Cl2
  3. customThe solution obtained
  4. concentrationwas concentrated
  5. customthe residue was recrystallized from EtOAc/Hexanes (5/1)

출처 및 근거

ORD 기록
ord-576e3dc1ea674f03bc26de2e591a35b7
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863293B2

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