3-Fluoroacetophenone → HCID 12988745, 화합물

HRID 354238

반응식

HRID 354238 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1)=[O:14].[H-].[Na+].[NH4+].[Cl-]>COCCOC>[F:21][C:17]1[CH:16]=[C:15]([C:13](=[O:14])[CH2:12][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=2)[CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 99673-FluoroacetophenoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 923422-Chloro-5-(trifluoromethyl)pyridine

생성물 1

HCID 12988745HCID 12988745, 화합물수율 84%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
42.5 °C

실험 절차

A reaction vessel was charged with 2-chloro-5-trifluoromethylpyridine (8 g, 44 mmol), 3-fluoroacetophenone (6.4 g, 46 mmol) and DME (56 ml). Sodium hydride (as a 60% oil dispersion, 5.8 g, 145 mmol) was added in portions to the mixture under nitrogen at room temperature. The mixture was stirred at 40-45° C. overnight. Upon the completion of the reaction, aqueous NH4Cl solution (240 ml) was added to the reaction mixture at room temperature. The mixture was stirred for 0.5 hr and filtered. The cake was washed with water, slurried in hexanes (32 ml) and dried in a vacuum oven to give 10.44 g (84%) of the title compound (a mixture of ketone and enol isomers) as a solid with purity 99% AUC by HPLC (Phenomenex Luna 3μ cyano, 100 mm×4.6 mm. Flow rate: 1 ml/min. UV detection: 220 nm. Eluent: 75% A, 25% B. A: 80/20/0.05 water/acetonitrile/TFA. B: 20/80/0.05 water/acetonitrile/TFA ).

후처리

  1. additionwas added to the reaction mixture at room temperature
  2. stirringThe mixture was stirred for 0.5 hr
  3. filtrationfiltered
  4. washThe cake was washed with water
  5. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-52a30f1acfa54175929863fcf3ffd3a6
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756498B2

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