Dimethylformamide → [2-Chloro-5-(methoxymethoxy)phenyl]acetonitrile

HRID 420550ノート

反応式

HRID 420550 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9]COC)=[CH:4][C:3]=1[CH3:13].Br[N:15]1C(=O)CC[C:16]1=O.[C-]#N.[Na+].CN(C)[CH:27]=[O:28]>C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:28][CH3:27])=[CH:4][C:3]=1[CH2:13][C:16]#[N:15]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 67184N-bromobutanimideHCID 22467254HCID 22467254、化合物

生成物 1

HCID 57966326[2-Chloro-5-(methoxymethoxy)phenyl]acetonitrile

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 5943Carbon Tetrachloride溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2-chloro-5-(methoxyethoxy)toluene (5.00 g; 26.8 mmol), N-bromosuccinimide (4.77 g; 26.8 mmol) and 2,2-azobis(isobutyronitrile) (0.09 g; 0.53 mmol) in carbon tetrachloride (25 ml) was refluxed for 2 hours. After air cooling and filtration the precipitate, the filtrate was condensed under reduced pressure. To the residue were added sodium cyanide (2.77 g; 80.4 mol) and anhydrous N,N-dimethylformamide (30 ml). The mixture was stirred at room temperature for 2 hours. Water and ethyl acetate were added to the reaction solution and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1→4:1) to give [2-chloro-5-(methoxymethoxy)phenyl]acetonitrile as colorless oil (2.64 g; 47%).

後処理

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter air cooling
  3. filtrationfiltration the precipitate
  4. customcondensed under reduced pressure
  5. extractionextracted
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1→4:1)

出典と根拠

ORDレコード
ord-eccd55db5c514dd491397726262db87f
出典データセット
uspto-grants-2012_01
特許番号
US08097610B2

反応ノート

読み込み中…