反应 #531806

ord-dd77b5c646954f9197777bd4683773f4

反应方程式

BrCc1ccccc1
Benzyl bromide
COc1cc(Br)c(C=O)cc1O
2-Bromo-5-hydroxy-4-methoxybenzaldehyde
O=C([O-])[O-].[K+].[K+]
K2CO3
CC#N
acetonitrile
COc1cc(Br)c(C=O)cc1OCc1ccccc1
2
收率 83.0%
COc1cc(Br)c(C=O)cc1OCc1ccccc1
5-Benzyloxy-2-bromo-4-methoxybenzaldehyde
收率 83.0%

溶剂

反应条件

温度
50°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他flushed with Ar
  2. 2
    温度After cooling
  3. 3
    萃取extracted with CH2Cl2 (300 mL)
  4. 4
    洗涤The CH2Cl2 was washed with water (3×100 mL)
  5. 5
    其他dried
  6. 6
    浓缩concentrated
  7. 7
    其他Recrystallization with isopropanol: water (3:1)

实验过程

2-Bromo-5-hydroxy-4-methoxybenzaldehyde (25 g, 0.108 mol) and K2CO3 (30 g, 0.216 mol) were added to acetonitrile (250 mL) and flushed with Ar. Benzyl bromide (20 g, 0.12 mol) was added and the mixture was heated under Ar for 20 h at 50° C. After cooling, the mixture was poured into water (200 ml) and extracted with CH2Cl2 (300 mL). The CH2Cl2 was washed with water (3×100 mL), dried and concentrated. Recrystallization with isopropanol: water (3:1) gave 28.8 g (83%) of 2 as a light brown solid. 1H-NMR (400 MHz, CDCl3) dH 3.96 (3H, s, OCH3), 5.16 (2H, s, CH2Ph), 7.07-7.48 (7H, m, ArH+CH2Ph), 10.16 (1H, s, CHO).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08475776B2uspto-grants-2013_07