3-Bromo-2-chloro-5-methylpyridine → 3-Bromo-2-ethoxy-5-methylpyridine

HRID 578820ノート

反応式

HRID 578820 の反応式
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[O-:10][CH2:11][CH3:12].[Na+]>C(O)C.O>[Br:1][C:2]1[C:3]([O:10][CH2:11][CH3:12])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

参加物

5

反応物 2

HCID 2854373-Bromo-2-chloro-5-methylpyridineHCID 2723922Sodium ethoxide

生成物 1

HCID 225911753-Bromo-2-ethoxy-5-methylpyridine収率 72%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-bromo-2-chloro-5-methylpyridine (4.00 g, 19.37 mmol) in ethanol (100 mL) was added sodium ethoxide (6.59 g, 96.9 mmol) in three portions. The mixture was stirred under nitrogen at 100° C. for 2 days. The reaction was cooled to room temperature, diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 20%, EtOAc/hexanes) afforded the title compound (3.00 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ 7.94 (dd, J=0.8, 2.3 Hz, 1H), 7.89-7.82 (m, 1H), 4.31 (q, J=7.0 Hz, 2H), 2.18 (t, J=0.8 Hz, 3H), 1.30 (t, J=7.0 Hz, 3H).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customthe solvent was removed under reduced pressure
  5. customPurification (FCC, SiO2, 20%, EtOAc/hexanes)

出典と根拠

ORDレコード
ord-a5a5aff655ce452c83686e53b2305a94
出典データセット
uspto-grants-2015_05
特許番号
US09040692B2

反応ノート

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