1,3-Dibromopropane → 1-(4-Bromo-2-fluorophenyl)cyclobutanecarbonitrile

HRID 1453061ノート

反応式

HRID 1453061 の反応式
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6]Br.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[C:11]([F:18])[CH:10]=1.[Cl-].[NH4+]>CS(C)=O.C(OCC)C.C(Cl)Cl>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:16]#[N:17])[CH2:6][CH2:5][CH2:4]2)=[C:11]([F:18])[CH:10]=1

参加物

8

反応物 4

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrile

生成物 1

HCID 587626531-(4-Bromo-2-fluorophenyl)cyclobutanecarbonitrile

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

To a slurry of NaH (1.64 g, 60% suspension in mineral oil, 41.1 mmol) in DMSO (19 mL) stirred at room temperature, was added a solution of 1,3-dibromopropane (2.1 mL, 20.6 mmol) and (4-Bromo-2-fluoro-phenyl)-acetonitrile (4.0 g, 18.7 mmol) in diethyl ether (10 mL) slowly keeping the temprature of the reaction between 25 degrees Celsius and 35 degrees Celsius. Stir for two hours after the addition is complete, and pour into saturated ammonium chloride (150 mL). Add 100 ml of CH2Cl2 and separate the layers. Extract the aqueous phase with 2×50 mL CH2Cl2 and combine the organics. After drying the organic liquid over MgSO4, the solids were removed by filtration, and the liquid was concentrated to an oil. The oil was purified by flash chromatography to yield the desired product. Yield: 1.43 g, 30%. MS (APCI) 254 (M+H), 256 (M+2+H).

後処理

  1. customthe temprature of the reaction between 25 degrees Celsius and 35 degrees Celsius
  2. additionafter the addition
  3. customseparate the layers
  4. extractionExtract the aqueous phase with 2×50 mL CH2Cl2
  5. dry with materialAfter drying the organic liquid over MgSO4
  6. customthe solids were removed by filtration
  7. concentrationthe liquid was concentrated to an oil
  8. customThe oil was purified by flash chromatography

出典と根拠

ORDレコード
ord-ebc1414a3bcd4591a60083956d7a6834
出典データセット
uspto-grants-2009_01
特許番号
US07473790B2

反応ノート

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