2-(Dimethylamino)ethanol → 2-Bromo-4-phenylpyridine

HRID 1158706

반응식

HRID 1158706 반응식
CN(C)CCO.C([Li])CCC.[C:12]1([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Br)(Br)(Br)[Br:25]>CCCCCC.O>[Br:25][C:22]1[CH:23]=[C:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:19]=[CH:20][N:21]=1

참가 물질

7

반응물 4

HCID 79022-(Dimethylamino)ethanolHCID 11205Carbon tetrabromideHCID 136514-PhenylpyridineHCID 178418339Butyllithium

생성물 1

HCID 1047002-Bromo-4-phenylpyridine수율 45.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8058Hexane용매3회

반응 조건

온도
0 °C

실험 절차

To a solution of 2-dimethylaminoethanol (5.60 g, 62.8 mmol) in hexane (80 ml) was added dropwise 1.6N hexane solution of n-butyl lithium (78.5 ml, 125 mmol) under ice-cooling, and stirred at 0° C. for 30 minutes. Then, 4-phenylpyridine (3.24 g, 20.8 mmol) was added thereto, and stirred at 0° C. for 1 hour. After cooling the reaction solution to −78° C., a solution of carbon tetrabromide (25.0 g, 75.4 mmol) in hexane (40 ml) was added thereto, and stirred at −78° C. for 1 hour, then at room temperature for 1 hour. To the reaction solution was added water under ice-cooling, and extracted with ether. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduce pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the titled compound 2.21 g (45.4%) as solid product.

후처리

  1. temperaturecooling
  2. stirringstirred at 0° C. for 1 hour
  3. temperatureAfter cooling the reaction solution to −78° C.
  4. stirringstirred at −78° C. for 1 hour
  5. waitat room temperature for 1 hour
  6. temperaturecooling
  7. extractionextracted with ether
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled away
  10. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-9d562519b434426ca73f9acfdde51242
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812025B2

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