Succinimide → 2-[2-(Bromomethyl)-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 2262405ノート

反応式

HRID 2262405 の反応式
[CH3:1][C:2]1[C:7]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:12])([CH3:11])[O:9]2)=[CH:6][C:5]([C:17]([F:20])([F:19])[F:18])=[CH:4][CH:3]=1.C1C(=O)N([Br:28])C(=O)C1.C1(=O)NC(=O)CC1>CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>[Br:28][CH2:1][C:2]1[C:7]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:11])([CH3:12])[O:9]2)=[CH:6][C:5]([C:17]([F:19])([F:18])[F:20])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 579349502-Methyl-5-trifluoroMethylphenylboronic acid, pinacol ester

生成物 1

HCID 1190066772-[2-(Bromomethyl)-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane収率 98.6%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

6-Methyl-3-(trifluoromethyl)phenylboronic acid pinacol ester (24b, 3.0 g, 10 mmol) and 60 ml CCl4 were placed in 500 ml round-bottom flask. NBS (1.9, 10.5 mmol, 1.05 eq) and AIBN (0.02 g, 0.14 mmol, 0.014 eq) were added and the reaction mixture was refluxed for 4.5 h in the presence of 75 W incandescent bulb. After 4.5 h the solution was cooled down to room temperature allowing the succinimide to precipitate out. The solid was filtered off. The solvent was removed and oily product was collected. The crude product was purified by triturating with hexane which resulted in 80% pure product (25b, 3.6 g, 95% yield).

後処理

  1. temperaturethe reaction mixture was refluxed for 4.5 h in the presence of 75 W incandescent bulb
  2. customto precipitate out
  3. filtrationThe solid was filtered off
  4. customThe solvent was removed
  5. customoily product was collected
  6. customThe crude product was purified
  7. customby triturating with hexane which

出典と根拠

ORDレコード
ord-d16e63e36486491fa8b12450f5c3bb42
出典データセット
uspto-grants-2010_12
特許番号
US07851225B2

反応ノート

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