Methyl iodide → 1-Bromo-3-(methoxymethyl)-5-nitrobenzene

HRID 410403

反応式

HRID 410403 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][OH:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.I[CH3:14].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][O:12][CH3:14])[CH:3]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14866972(3-Bromo-5-nitrophenyl)methanol

生成物 1

HCID 672485781-Bromo-3-(methoxymethyl)-5-nitrobenzene収率 89%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of (3-bromo-5-nitrophenyl)methanol (500 mg, 2.155 mmol) in DMF (7.2 mL) was added iodomethane (0.40 mL, 6.46 mmol. The solution was cooled to 0° C. before NaH (60% dispersion in mineral oil, 172 mg, 4.31 mmol) was added. The reaction was stirred at 0° C. and allowed to come to room temperature. After 2 hours the reaction was quenched with water and ethyl acetate was then added. Extraction was done with ethyl acetate (3×). The combined organic layer was dried over magnesium sulfate and then filtered. Ethyl acetate was then removed in vacuo to afford 1-bromo-3-(methoxymethyl)-5-nitrobenzene (470 mg, 1.910 mmol, 89% yield) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.25 (s, 1H), 8.13 (s, 1H), 7.96 (s, 1H), 4.53 (s, 2H), 3.33 (s, 3H).

後処理

  1. additionwas added
  2. customto come to room temperature
  3. customAfter 2 hours the reaction was quenched with water and ethyl acetate
  4. additionwas then added
  5. extractionExtraction
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customEthyl acetate was then removed in vacuo

出典と根拠

ORDレコード
ord-73b038df3e394e14adf20762efe2023a
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

関連ノート

読み込み中…