Water → 6-Bromo-3-isopropoxy-2-methylpyridine

HRID 1478456노트

반응식

HRID 1478456 반응식
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([OH:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:17]([CH3:19])[CH3:18].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([O:9][CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 111947876-Bromo-2-methylpyridin-3-ol

생성물 1

HCID 866685246-Bromo-3-isopropoxy-2-methylpyridine수율 84.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

6-Bromo-2-methylpyridin-3-ol (10.5 g, 55.9 mmol) was dissolved in DMF (100 mL). K2CO3 (19.3 g, 139.6 mmol) and 2-bromopropane (13.1 ml, 139.6 mmol) were added to the solution and the mixture was heated at 100° C. overnight. The mixture was poured into a mixture of water and EtOAc (200 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried (Na2SO4) and concentrated. The crude oil was purified by column chromatography (0-20% ethyl acetate/heptanes) to give 6-bromo-3-isopropoxy-2-methylpyridine (10.9 g, 85) as a yellow oil. 1H-NMR (300 MHz, CDCl3) 1.42 (d, 6H), 2.48 (s, 3H), 4.65 (m, 1H), 7.20 (d, 1H), 8.04 (d, 1H).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude oil was purified by column chromatography (0-20% ethyl acetate/heptanes)

출처 및 근거

ORD 기록
ord-3266bae92704430d9f39c81356968db5
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403839B2

반응 노트

불러오는 중…