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Imidazole → 4-((Tert-butyldimethylsilyl)oxy)-2-fluorobenzonitrile

HRID 1678702
ノート
印刷プレビュー

反応式

HRID 1678702 の反応式
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].N1C=CN=C1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C>[Si:20]([O:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27346752-Fluoro-4-hydroxybenzonitrile

生成物 1

HCID 593707824-((Tert-butyldimethylsilyl)oxy)-2-fluorobenzonitrile収率 73%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

2-Fluoro-4-hydroxybenzonitrile (30.1 g; manufactured by Wako Pure Chemical Industries, Ltd.) and imidazole (18.3 g; manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in dehydrated DMF (436 mL; manufactured by Kanto Chemical Co., Inc.), and the solution was cooled to 0° C. Subsequently, TBDMSCl (48.3 g; manufactured by Tokyo Chemical Industry Co., Ltd.) was added thereto, and the mixture was stirred for one hour while the temperature was raised to room temperature. The solvent was evaporated under reduced pressure from the reaction solution, subsequently water was added thereto, and the mixture was extracted two times with ethyl acetate. The organic layer was washed two times with water and with brine, and was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by column chromatography (“COLUMN-A.”; n-hexane:ethyl acetate=100:0→94:6). Thus, the title compound (40.3 g) was obtained.

後処理

  1. temperaturewas raised to room temperature
  2. customThe solvent was evaporated under reduced pressure from the reaction solution, subsequently water
  3. additionwas added
  4. extractionthe mixture was extracted two times with ethyl acetate
  5. washThe organic layer was washed two times with water
  6. dry with materialwith brine, and was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by column chromatography (“COLUMN-A.”; n-hexane:ethyl acetate=100:0→94:6)

出典と根拠

ORDレコード
ord-d59687f4c8524911b17402b0c2ad2e5b
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08008506B2

反応ノート

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