2-Bromo-5-iodo-3-methylpyridine → 5-Iodo-2-methoxy-3-methylpyridine

HRID 1432874

반응식

HRID 1432874 반응식
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([I:9])=[CH:4][N:3]=1.[CH3:10][O-:11].[Na+]>CS(C)=O.C(OCC)C.O>[I:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([O:11][CH3:10])=[N:3][CH:4]=1

참가 물질

6

반응물 2

HCID 101086802-Bromo-5-iodo-3-methylpyridineHCID 10942334Sodium Methoxide

생성물 1

HCID 534159905-Iodo-2-methoxy-3-methylpyridine수율 71.8%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

To a solution containing 2-bromo-5-iodo-3-methyl-pyridine (4.80 g, 16.0 mmol) in DMSO (15 mL) is added methanolic NaOMe (3.33 M, 5.3 mL, 17.7 mmol) at 0° C. The solution is allowed to warm to ambient temperature and then heated at 70° C. for 1 hour. The reaction mixture is diluted with diethyl ether (300 mL) and water (200 mL) and the layers are separated. The organic phase is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude product is purified by silica gel flash column chromatography (hexane/diethyl ether, 19:1) to provide 2.86 g (71%) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3) δ2.12 (s, 3H), 3.90 (s, 3H), 7.60 (d, J=2.1 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H) ppm; MS (EI): m/z 249 (M+).

후처리

  1. temperatureheated at 70° C. for 1 hour
  2. customthe layers are separated
  3. washThe organic phase is washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel flash column chromatography (hexane/diethyl ether, 19:1)

출처 및 근거

ORD 기록
ord-1e6d615f5fbe42699a7390bfa217cf1d
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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