2-(Dimethylamino)ethanol → 2-Bromo-6-phenylpyridine

HRID 659099

반응식

HRID 659099 반응식
CN(C)CCO.C([Li])CCC.[C:12]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Br)(Br)(Br)[Br:25]>CCCCCCC.O>[Br:25][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:19]=1

참가 물질

7

반응물 4

HCID 79022-(Dimethylamino)ethanolHCID 11205Carbon tetrabromideHCID 138872-PhenylpyridineHCID 178418339Butyllithium

생성물 1

HCID 5686792-Bromo-6-phenylpyridine

시약·촉매·용매 2

HCID 962Water용매HCID 8900Heptane용매2회

반응 조건

온도
-78 °C

실험 절차

To N,N-dimethylethanolamine (0.8 mL, 8.00 mmol) in heptane (10 mL) cooled externally to 0° C. was added dropwise a 2.5 M n-butyllithium solution (6.40 mL) and the reaction mixture stirred for 30 minutes. 2-Phenylpyridine (12) (412 mg, 2.66 mmol) in heptane (5 mL) was then added and the reaction mixture stirred for a further 1 hour. The reaction was then cooled and carbon tetrabromide (3.18 g, 9.60 mmol) was added whilst maintaining the temperature at −78° C. The reaction was kept at −78° C. for 1 hour and then allowed to warm to ambient temperature. Water was cautiously added and extracted with TBME (×2), dried (Na2SO4) and the solvent concentrated in vacuo. The crude product was purified by column chromatography eluting with 5% EtOAc in heptane to give the title compound. Yield: 300 mg, 48%; LC-MS tr 1.63 min; HPLC Purity: 97%; MS (ES+) m/z 234, 236 (M+H)

후처리

  1. stirringthe reaction mixture stirred for a further 1 hour
  2. temperatureThe reaction was then cooled
  3. waitThe reaction was kept at −78° C. for 1 hour
  4. temperatureto warm to ambient temperature
  5. extractionextracted with TBME (×2)
  6. dry with materialdried (Na2SO4)
  7. concentrationthe solvent concentrated in vacuo
  8. customThe crude product was purified by column chromatography
  9. washeluting with 5% EtOAc in heptane

출처 및 근거

ORD 기록
ord-65c3036df0ef4a609ae2dc80275f93d8
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080567B2

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