Hydrochloric Acid → 3-[(2,3-Difluoro-6-nitrophenyl)oxy]-5-(methyloxy)benzonitrile

HRID 1875240노트

반응식

HRID 1875240 반응식
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:7]#[N:8].[F:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17](F)[C:16]=1[F:25].Cl>C1COCC1>[F:25][C:16]1[C:15]([F:14])=[CH:20][CH:19]=[C:18]([N+:21]([O-:23])=[O:22])[C:17]=1[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:7]#[N:8]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 698711,2,3-Trifluoro-4-nitrobenzeneHCID 229962023-Hydroxy-5-methoxybenzonitrile

생성물 1

HCID 687222673-[(2,3-Difluoro-6-nitrophenyl)oxy]-5-(methyloxy)benzonitrile수율 92.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

NaH (2.05 g, 51.2 mmol) was added portionwise to a 0° C. solution of 3-hydroxy-5-(methyloxy)benzonitrile (7.63 g, 51.2 mmol) (prepared following the procedure in Magano et al. J. Org. Chem. 2006, 71, 7103) in THF (205 ml). When addition was complete, the thick suspension was stirred at this temperature for another 30 mins, and trifluoronitrobenzene (9.51 g, 53.7 mmol) was then added. The reaction mixture was stirred at RT for 3 h, dilute HCl was added and the solution was extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, evaporated and purified by silica gel chromatography (0-30% EtOAc/hexanes) to afford the title compound (14.44 g, 92%) as a light yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.96 (ddd, J=9.36, 4.97, 2.24 Hz, 1H) 7.28-7.35 (m, 1H) 6.95 (d, J=0.73 Hz, 1H) 6.78 (t, J=2.15 Hz, 1H) 6.73 (s, 1H) 3.85 (s, 3H).

후처리

  1. customprepared
  2. additionWhen addition
  3. stirringThe reaction mixture was stirred at RT for 3 h
  4. extractionthe solution was extracted with EtOAc
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by silica gel chromatography (0-30% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-73620ff5ede249ffaffdcb6c45f97147
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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