Benzyl chloroformate → benzyl N-(4-bromo-2-methoxyphenyl)carbamate

HRID 432169

反応式

HRID 432169 の反応式
C(=O)(O)[O-].[Na+].[Br:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([O:14][CH3:15])[CH:8]=1.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>O.O1CCOCC1>[Br:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][C:17](=[O:18])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:9]([O:14][CH3:15])[CH:8]=1

参加物

6

反応物 3

HCID 10387Benzyl chloroformateHCID 4592574-Bromo-2-methoxyanilineHCID 516892Sodium Bicarbonate

生成物 1

HCID 22346837benzyl N-(4-bromo-2-methoxyphenyl)carbamate収率 74.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of sodium bicarbonate (3.12 g, 0.0371 mol) in water (35 mL) was added to a solution of 4-bromo-2-methoxyaniline (3.00 g, 0.0148 mol) in dioxane (50 mL). The resulting mixture was stirred for 5 minutes and benzyl chloroformate (3.8 g, 0.022 mol) was added dropwise over 3 minutes. The reaction mixture was for two hours, then dioxane was removed under reduced pressure and the water phase was extracted twice with ethyl acetate (100 mL each). The combined organic extracts were dried over magnesium sulfate and after filtration concentrated under reduced pressure. The resulting residue was purified by flash chromatography on silica using ethyl acetate/n-heptane (5:95) as mobile phase to yield benzyl N-(4-bromo-2-methoxyphenyl)carbamate (3.75 g, 0.011 mol) as a white solid: 1H NMR (DMSO-d6, 400 MHz) 8.72 (s, 1H), 7.61 (d, 1H), 7.38 (m, 5H), 7.20 (s, 1H), 7.10 (d, 1H), 5.14 (s, 2H), 3.81 (s, 3H). TLC (ethyl acetate/heptane 1:9) Rf 0.21.

後処理

  1. waitThe reaction mixture was for two hours
  2. customdioxane was removed under reduced pressure
  3. extractionthe water phase was extracted twice with ethyl acetate (100 mL each)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationafter filtration
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by flash chromatography on silica

出典と根拠

ORDレコード
ord-711581551b3f4498b6a374c6f81df232
出典データセット
uspto-grants-2003_12
特許番号
US06660744B1

関連ノート

読み込み中…