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

HRID 1592658ノート

反応式

HRID 1592658 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-19ecddc462ce41858596f49969b292a3
出典データセット
uspto-grants-2007_11
特許番号
US07291631B2

反応ノート

読み込み中…