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

HRID 1432874

反応式

HRID 1432874 の反応式
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

参加物

6

反応物 2

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

生成物 1

HCID 534159905-Iodo-2-methoxy-3-methylpyridine収率 71.8%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-1e6d615f5fbe42699a7390bfa217cf1d
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

関連ノート

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