Azobisisobutyronitrile → 2-[2-(Bromomethyl)-5-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1097184ノート

反応式

HRID 1097184 の反応式
[F:1][C:2]1[CH:3]=[C:4]([B:9]2[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]2)[C:5]([CH3:8])=[CH:6][CH:7]=1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[Br:25][CH2:8][C:5]1[C:4]([B:9]2[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]2)=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1

参加物

6

反応物 4

HCID 6547AzobisisobutyronitrileHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 790162605-Fluoro-2-Methylbenzeneboronic acid pinacol ester, 97%

生成物 1

HCID 532171032-[2-(Bromomethyl)-5-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane収率 84%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

3-Fluoro-6-methylphenylboronic acid pinacol ester (29a, 5.01 g, 21.2 mmol) and 140 ml CCl4 were placed in 500 ml round-bottom flask. NBS (3.97 g, 22.3 mmol, 1.05 eq) and AIBN (0.054 g, 0.33 mmol, 0.016 eq) were added and the reaction mixture was refluxed for 3.5 h in the presence of 75 W incandescent bulb. After 3.5 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. Purification with column chromatography (95/5 Hexanes/Ethyl acetate) resulted in pure product (30a, 5.59 g, 84% yield).

後処理

  1. temperaturethe reaction mixture was refluxed for 3.5 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. customPurification with column chromatography (95/5 Hexanes/Ethyl acetate)

出典と根拠

ORDレコード
ord-ce89ff158d77471692c6d8b2de96ecc9
出典データセット
uspto-grants-2012_03
特許番号
US08143068B2

反応ノート

読み込み中…