Ammonium Chloride → 3-Chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile

HRID 1370022

反応式

HRID 1370022 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[Cl:10][CH2:11][C:12]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].[Cl-].[NH4+].C(OCC)(=O)C.CCCCCC>O1CCCC1>[Cl:10][CH2:11][C:12]1[CH:20]=[C:19]([CH:18]=[CH:17][C:13]=1[C:14](=[O:15])[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:21]#[N:22]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 113449102-(Chloromethyl)-4-cyanobenzoyl chlorideHCID 21226206Ethyl acetate hexaneHCID 178418676HCID 178418676、化合物

生成物 1

HCID 99434343-Chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 4-fluoro phenylmagnesium bromide (3.76 g) in tetrahydrofuran (15ml) was added to a cooled solution of 2-chloromethyl-4-cyano-benzoyl chloride (3.95 g) in tetrahydrofuran (10 ml) so that the temperature did not raise above 0° C. The mixture was warmed slowly to room temperature and stirred over night. Saturated ammonium chloride solution (60 ml) was added and stirring continued for 0.5 hours. The phases were separated and the aqueous phase was extracted with diethylether (30 ml). The combined organic phases were dried over sodium sulfate, filtered and dried in vacuo to give a brown solid. Flash chromatography (ethyl acetate/n-hexane=1/10) provided the product as colourless solid. Yield 2.95 g, 58%. 1H NMR (CDCl3, 400 MHz): 4.71 (2H, s), 7.16-7.21 (2H, m), 7.46 (1H, d, J=7.9 Hz), 7.71 (1H, dd, J=1.5, 7.9 Hz), 7.81-7.86 (2H, m), 7.89 (1H, d, J=1.5 Hz). 13C NMR (CDCl3, 100 MHz): 42.3, 115.0, 116.4, 116.6, 117.9, 129.6, 132.95, 132.98, 133.4, 133.5, 134.3, 138.7, 142.4, 165.5, 168.1, 194.5.

後処理

  1. temperaturedid not raise above 0° C
  2. stirringstirring
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with diethylether (30 ml)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customdried in vacuo
  8. customto give a brown solid

出典と根拠

ORDレコード
ord-fe5229203e074708b1a8d6bfe891091e
出典データセット
uspto-grants-2003_06
特許番号
US06579993B2

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