1-Bromo-2,4-dimethoxybenzene → HCID 44610346, 화합물

HRID 1432514노트

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HRID 1432514 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1Br.C([Li])CCC.[I-].[CH3:18][N+:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1>C(OCC)C.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:24]1[CH:23]=[C:22]([CH3:25])[CH:21]=[CH:20][N:19]1[CH3:18]

참가 물질

6

반응물 3

HCID 872661-Bromo-2,4-dimethoxybenzeneHCID 2006031,4-Dimethylpyridinium IodideHCID 178418339Butyllithium

생성물 1

HCID 44610346HCID 44610346, 화합물수율 93%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

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온도
-78 °C

실험 절차

To a stirred solution of 2,4-dimethoxybromobenzene (1) (0.5 g, 2.3 mmol) in diethyl ether (10 ml) cooled at −78° C. under nitrogen was added a solution of n-butyl lithium (1.0 ml, 2.5 mmol of 2.5M solution in hexane) drop wise. The mixture was stirred at −78° C. for 2 hours and then 1,4-dimethyl pyridinium iodide (2) (0.54 g, 2.5 mmol) was added as a solid. The resultant mixture was allowed to warm to room temperature and stirred at room temperature for 18 hours. The mixture was diluted with water (20 ml) and extracted with diethyl ether (2×15 ml). The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated to yield 2-(2,4-dimethoxyphenyl)-1,4-dimethyl-1,2-dihydropyridine (4) (0.5 g, 93%) as a brown oil, 1H NMR CDCl3 ??1.7 (s, 3H), 2.7 (s, 3H), 3.8 (s, 6H), 4.45 (dd, 1H, J=2.7) 4.85 (m, 1H), 5.4 (d, 1H, J=4), 6.05 (d, 1H, J=7), 6.45 (d, 1H, J=3), 6.55 (m, 1H), 7.5 (d, 1H, J=9).

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for 18 hours
  3. extractionextracted with diethyl ether (2×15 ml)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-377eb92d91034d5a9511960163134692
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612101B2

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