Water → 4-Bromo-2-nitroanisole

HRID 1166236

反応式

HRID 1166236 の反応式
[Br:1]Br.[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])([O-:5])=[O:4].O>C(O)(=O)C>[Br:1][C:10]1[CH:9]=[CH:8][C:7]([O:12][CH3:13])=[C:6]([N+:3]([O-:5])=[O:4])[CH:11]=1

参加物

5

反応物 3

HCID 962WaterHCID 70482-NitroanisoleHCID 24408Bromine2 回

生成物 1

HCID 1185334-Bromo-2-nitroanisole収率 87%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
60 °C

実験手順

Bromine, Br2 (16 ml, 311 mmol) was added in small portions to a solution of 2-nitroanisole (17.1 ml, 140 mmol) in glacial acetic acid (80 ml). The reaction mixture was then heated at 60° C. for one hour. The reaction was poured into 400 ml water, and extracted with 600 ml diethyl ether/600 ml saturated NaHSO3 (aqueous). The organic layer was washed with NaHSO3 solution, then with water, dried over sodium sulfate, and concentrated under vacuum. The residue was recrystallized from diethyl ether to give 28.4 g (87%) of 4-bromo-2-nitroanisole. 1H NMR (300 MHz, CDCl3) δ7.970 (1H, d, J=2.5 Hz), 7.64 (1H, dd, J=8.9, 2.4 Hz), 7.00 (1H, d, J=8.9 Hz), 3.96 (3H, s).

後処理

  1. extractionextracted with 600 ml diethyl ether/600 ml saturated NaHSO3 (aqueous)
  2. washThe organic layer was washed with NaHSO3 solution
  3. dry with materialwith water, dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was recrystallized from diethyl ether

出典と根拠

ORDレコード
ord-85b6ee239fb3408888e6833904d64cac
出典データセット
uspto-grants-2003_09
特許番号
US06613786B2

関連ノート

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