反应 #671437

反应方程式

hydrochloric acid

2-methoxy-3,5-di-tert-butylphenylboronic acid

3-bromocinnamic acid

potassium carbonate

→

3-(3′,5′-di-tert-butyl-2′-methoxy-3-biphenylyl)acrylic Acid

溶剂

ethyl acetate

Water

DME

反应条件

后处理

1. 1
   其他the reaction medium was degassed
2. 2
   温度the mixture was refluxed for 20 hours
3. 3
   其他The organic phase was separated out
4. 4
   洗涤washed with water
5. 5
   干燥dried over magnesium sulfate
6. 6
   其他evaporated
7. 7
   其他The residue obtained
8. 8
   其他was purified by chromatography on a column of silica
9. 9
   洗涤eluted with a mixture of heptane and ethyl acetate (75/25)
10. 10
    其他After evaporation of the solvents, 990 mg (66%) of 3-(3′,5′-di-tert-butyl-2′-methoxy-3-biphenylyl)acrylic acid having a melting point of 182°-3° C.
11. 11
    其他were collected

实验过程

2.2 g (8.3 mmol) of 2-methoxy-3,5-di-tert-butylphenylboronic acid, 942 mg (4.15 mmol) of 3-bromocinnamic acid and 70 ml of DME were introduced into a three-necked flask under a stream of nitrogen. 11.4 ml of aqueous potassium carbonate solution (2M) were added dropwise and the reaction medium was degassed. 144 mg (0.12 mmol) of tetrakistriphenylphosphinepalladium(0) were then added and the mixture was refluxed for 20 hours. Water and ethyl acetate were added to the reaction medium and this mixture was acidified to pH 1 with hydrochloric acid. The organic phase was separated out after settling had taken place, washed with water, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (75/25). After evaporation of the solvents, 990 mg (66%) of 3-(3′,5′-di-tert-butyl-2′-methoxy-3-biphenylyl)acrylic acid having a melting point of 182°-3° C. were collected.

来源