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

HRID 72922노트

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HRID 72922 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 85%

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 reaction mixture was heated at 100° C. overnight. The reaction mixture was poured onto 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 in vacuo. The crude oil was purified by silica gel 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 in vacuo
  5. customThe crude oil was purified by silica gel column chromatography (0-20% ethyl acetate/heptanes)

출처 및 근거

ORD 기록
ord-4230d3130cd940e6a25e34a934d55773
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828996B2

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