Carbon Dioxide → 2-Fluoro-5-(trifluoromethoxy)benzaldehyde

HRID 1786218노트

반응식

HRID 1786218 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[C:18](=O)=[O:19].CN(C=O)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]([F:10])([F:11])[F:12])=[CH:6][C:7]=1[CH:18]=[O:19]

참가 물질

6

반응물 4

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 676984-(Trifluoromethoxy)fluorobenzeneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 27833242-Fluoro-5-(trifluoromethoxy)benzaldehyde수율 53%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-fluoro-4-trifluoromethoxy-benzene (21.0 g, 117 mmol) in THF (233 mL) was cooled to <−70° C. and tert.-butyllithium (86 mL, 1.5 M in pentane, 129 mmol) was added at such a rate that temperature was kept <−70° C. Stirring in the dry ice bath was continued for 15 min, then DMF (11.6 mL, 150 mmol) was added dropwise keeping temperature <−70° C. After 30 min the reaction mixture was allowed to reach rt, quenched with saturated NH4Cl solution and extracted with diethylether. The organic phase was washed with brine, concentrated and chromatographed (SiO2, heptanes:ethyl acetate=100:0 to 80:2) to afford the title compound (11.0 g, 53%) as a light yellow oil. 1H-NMR (300 MHz, DMSO): δ=7.60 (t, J=9.2 Hz, 1H), 7.75-7.85 (m, 2H), 10.20 (s, 1H).

후처리

  1. customwas kept <−70° C
  2. customtemperature <−70° C
  3. waitAfter 30 min the reaction mixture was allowed
  4. customto reach rt
  5. customquenched with saturated NH4Cl solution
  6. extractionextracted with diethylether
  7. washThe organic phase was washed with brine
  8. concentrationconcentrated
  9. customchromatographed (SiO2, heptanes:ethyl acetate=100:0 to 80:2)

출처 및 근거

ORD 기록
ord-953fd019dabd4558a10ba291c9bfb23d
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507729B2

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