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

HRID 1370022

반응식

HRID 1370022 반응식
[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]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 113449102-(Chloromethyl)-4-cyanobenzoyl chlorideHCID 21226206Ethyl acetate hexaneHCID 178418676HCID 178418676, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fe5229203e074708b1a8d6bfe891091e
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06579993B2

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