2-Tert-Butylphenol → Pyridine, 2-[2-(1,1-dimethylethyl)phenoxy]-3-nitro-

HRID 555390ノート

反応式

HRID 555390 の反応式
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)([CH3:14])([CH3:12])[CH3:13]

参加物

6

反応物 3

HCID 69232-Tert-ButylphenolHCID 10796Cesium carbonateHCID 796132-Chloro-3-nitropyridine

生成物 1

HCID 59857513Pyridine, 2-[2-(1,1-dimethylethyl)phenoxy]-3-nitro-収率 90.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A solution of 2-chloro-3-nitropyridine (21.05 g, 132.7 mmol) in DMF (100 mL) was treated with 2-tert-butylphenol (23.5 mL, 152.6 mmol) and cesium carbonate (129.8 g, 398.3 mmol). The mixture was heated at 80° C. for 30 h. The reaction was cooled to rt, and the mixture was poured in water (1 L) with stirring. The yellow precipitate formed was filtered and washed with water, and recrystallized from ethanol to afford 1a as beige crystals (32.83 g, 90%). 1H NMR (400 MHz, CD3OD) δ ppm 1.34 (s, 9H), 6.93 (m, 1H), 7.22 (m, 3H), 7.47 (m, 1H), 8.31 (dd, J=4.82, 1.75 Hz, 1H), 8.46 (dd, J=7.89, 1.75 Hz, 1H).

後処理

  1. temperatureThe reaction was cooled to rt
  2. customThe yellow precipitate formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-6819d368475344b7b7504e5e49d13ab9
出典データセット
uspto-grants-2011_11
特許番号
US08053450B2

反応ノート

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