反应 #302846

ord-225c1dd216054c80a40c00a970cdc7b6

反应方程式

Cl
hydrochloric acid
CC(=O)c1cc(Br)ccc1O
5′-bromo-2′-hydroxyacetophenone
CC(=O)c1cc(Br)ccc1O
compound 1
CC(=O)c1cc(Br)ccc1O
5′-bromo-2′-hydroxyacetophenone
O=C(Cl)c1ccc([N+](=O)[O-])cc1
4-nitrobenzoyl chloride
CC(=O)c1cc(Br)ccc1OC(=O)c1ccc([N+](=O)[O-])cc1
compound 2
CC(=O)c1cc(Br)ccc1OC(=O)c1ccc([N+](=O)[O-])cc1
4-nitrobenzoic acid 2-acetyl-4-bromophenyl ester

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The obtained mixture was reacted at room temperature for 30 minutes
  2. 2
    温度under cooling on ice
  3. 3
    过滤The obtained precipitate was collected by filtration
  4. 4
    洗涤the filtrate was then washed with purified water

实验过程

5′-bromo-2′-hydroxyacetophenone (compound 1) (863 mg, 4.65 mmol) was added to a pyridine solution (20 ml) that contained 4-nitrobenzoyl chloride (1.00 g, 4.65 mmol) in an ice bath. The obtained mixture was reacted at room temperature for 30 minutes, and the reaction solution was then poured into 1 N hydrochloric acid under cooling on ice. The obtained mixture was intensively stirred. The obtained precipitate was collected by filtration, and the filtrate was then washed with purified water, so as to obtain a product of interest, 4-nitrobenzoic acid 2-acetyl-4-bromophenyl ester (compound 2). Yield: 1.57 g (yield constant: 92.7%) 1H NMR (300 MHz, CDCl3) δ 8.37 (s, 4H), 8.00 (s, 1H), 7.76-7.72 (m, 1H), 7.16 (d, J=8.7 Hz, 1H), 2.55 (s, 3H). MS m/z 365 (MH+).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08192717B2uspto-grants-2012_06