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

HRID 63252

反応式

HRID 63252 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e8fee109147d4865ad47f6b30b8a68c8
出典データセット
uspto-grants-2016_09
特許番号
US09447073B2

関連ノート

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