Benzene, 1-fluoro-2-(trifluoromethyl)- → HCID 72765826, 화합물

HRID 971175

반응식

HRID 971175 반응식
C(O[K])(C)(C)C.[CH2:7]([O:9][C:10](=[N:12][OH:13])[CH3:11])[CH3:8].F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([F:24])([F:23])[F:22]>CN(C=O)C>[CH2:7]([O:9][C:10](=[N:12][O:13][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([F:24])([F:23])[F:22])[CH3:11])[CH3:8]

참가 물질

5

반응물 3

HCID 9807Benzene, 1-fluoro-2-(trifluoromethyl)-HCID 99894Ethyl acetohydroximateHCID 178418922HCID 178418922, 화합물2회

생성물 1

HCID 72765826HCID 72765826, 화합물수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Prepared using a procedure adapted from Miyazawa et al. (Miyazawa, E.; et al. Org. Prep. Proced. Int. 1997, 29, 594-600) tBuOK (0.78 g, 6.7 mmol) was added to a stirring solution of ethyl-N-hydroxyacetimidate (1.00 g, 6.06 mmol) in anhydrous DMF (6 mL) at 0° C. under an Ar atmosphere. After tBuOK addition was completed the reaction was stirred at room temperature. After 30 min 2-fluorobenzotrifluoride (1.29 mL, 6.06 mmol) was added and the reaction was heated at 80° C. for 2 h. Upon cooling the reaction mixture was diluted with ice water (100 mL) and extracted with EtOAc (3×40 mL). The combined organic layers were washed with brine (2×50 mL), dried with MgSO4, and concentrated to afford a dark oil. Flash chromatographic purification over silica (10% EtOAc in hexanes) afforded 15 as a clear liquid (1.33 g, 89%). 1H-NMR (500 MHz, CDCl3) δ 1.36 (t, J=7.1 Hz, 3H), 2.15 (s, 3H), 4.20 (q, J=7.1 Hz, 2H), 6.99 (apparent t, J=7.5 Hz, 1H), 7.47 (apparent dt, J=7.9 Hz, 1H), 7.52-7.57 (m, 2H); 13C-NMR (125 MHz, CDCl3) δ 14.3, 14.5, 63.2, 114.2, 116.2 (q, JC-F=31 Hz), 120.3, 123.7 (q, JC-F=272 Hz), 126.4 (q, JC-F=4.8 Hz), 133.2, 157.2 (q, JC-F=1.9 Hz), 167.1; LC-MS 248 m/z[MH]+, C11H13F3NO2 requires 248.

후처리

  1. customPrepared
  2. temperaturethe reaction was heated at 80° C. for 2 h
  3. temperatureUpon cooling the reaction mixture
  4. extractionextracted with EtOAc (3×40 mL)
  5. washThe combined organic layers were washed with brine (2×50 mL)
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customto afford a dark oil
  9. customFlash chromatographic purification over silica (10% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-948c527d9f0d4b3ba14a4b618fa6f0b0
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312361B2

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