Sodium Cyanide → HCID 66967418、化合物

HRID 926239ノート

反応式

HRID 926239 の反応式
[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.BrCC1C=CC=C(Cl)C=1OC.[C-]#N.[Na+]>CCO.CCOCC>[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 8929Sodium CyanideHCID 17989277(3-Chloro-2-methoxyphenyl)acetonitrileHCID 19390097HCID 19390097、化合物

生成物 1

HCID 66967418HCID 66967418、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

2-(3-chloro-2-methoxyphenyl)acetonitrile. A solution of 1-(bromomethyl)-3-chloro-2-methoxybenzene (30.8 g, 131 mmol) in EtOH (150 mL) at RT and under N2 was treated with an aq. solution of NaCN (12.8 g, 262 mmol in 50 mL H2O) and the mixture was heated to 100° C. for 3 h. The reaction was then cooled to RT and taken up in Et2O. The mixture was washed with H2O and brine, and the aq. phase was extracted again with Et2O. The combined org. layers dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1) to afford the title compound (15.8 g) as brown oil. UPLC (2 min) rt 1.383.

後処理

  1. temperatureThe reaction was then cooled to RT
  2. washThe mixture was washed with H2O and brine
  3. extractionthe aq. phase was extracted again with Et2O
  4. dry with materiallayers dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (SiO2, Hexane to Hexane/AcOEt 4:1)

出典と根拠

ORDレコード
ord-c416148c73b5435da5e14434576f3745
出典データセット
uspto-grants-2016_03
特許番号
US09284331B2

反応ノート

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