Potassium Carbonate → 4-((6-Bromopyridin-3-yl)oxy)benzonitrile

HRID 63252

반응식

HRID 63252 반응식
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 27628652-Bromo-5-hydroxypyridine

생성물 1

HCID 451422674-((6-Bromopyridin-3-yl)oxy)benzonitrile수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 6-bromopyridin-3-ol (10 g, 57.80 mmol) in DMF (60 mL) was added 4-fluorobenzonitrile (6.99 g, 57.8 mmol) and K2CO3 (11.9 g, 86.70 mmol) and the reaction mixture was stirred at 80° C. for 16 hours (h). The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated. The crude product was purified by column chromatography (silica gel, 100-200 mesh) to obtain the title compound as an off-white solid (10 g, 63%): mp 113° C.; 1H NMR (400 MHz, CDCl3) δ 8.22 (d, J=2.9 Hz, 1H), 7.70-7.63 (m, 2H), 7.56-7.51 (m, 1H), 7.28 (dd, J=8.5, 2.9 Hz, 1H), 7.10-7.02 (m, 2H); EIMS m/z 275.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, 100-200 mesh)

출처 및 근거

ORD 기록
ord-e8fee109147d4865ad47f6b30b8a68c8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447073B2

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