o-Bromocumene → isopropylbenzonitrile

HRID 1466436ノート

反応式

HRID 1466436 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:10])[CH3:9].[C:11]([Cu])#[N:12]>CN(C=O)C>[CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[N:12])([CH3:10])[CH3:9]

参加物

4

反応物 2

HCID 23475o-BromocumeneHCID 178418546HCID 178418546、化合物

生成物 1

HCID 10920642isopropylbenzonitrile収率 82%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a dry, N2 purged 100 mL round bottom flask attached with condenser was added 1-bromo-2-isopropylbenzene (10.0 g, 50.2 mmol), anhydrous DMF (26 mL), and CuCN (5.85 g, 653 mmol) The reaction slurry was stirred at reflux under N2 for 4 hrs prior to analysis by GCMS. The reaction mixture was cooled to room temperature and poured into an ice/aq NH4Cl solution. The resulting precipitates were removed by vacuum filtration through a Buchner funnel. The aqueous filtrate was extracted with EtOAc (150 mL×3). The combined organic phase was dried over Na2SO4, filtered and concentrated on the Rotavapor to afford 5.97 g (82% yield) of 2-isopropylbenzonitrile. The product was used in the next step without further purification. GCMS m/z=145 [M+].

後処理

  1. customTo a dry, N2 purged 100 mL round bottom flask
  2. customattached with condenser
  3. temperatureat reflux under N2 for 4 hrs
  4. customThe resulting precipitates
  5. customwere removed by vacuum filtration through a Buchner funnel
  6. extractionThe aqueous filtrate was extracted with EtOAc (150 mL×3)
  7. dry with materialThe combined organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated on the Rotavapor

出典と根拠

ORDレコード
ord-4004a327901144e88be26f715657d6eb
出典データセット
uspto-grants-2015_04
特許番号
US09000022B2

反応ノート

読み込み中…