Реакция #1075212

Уравнение реакции

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

Растворители

ethyl acetate

Water

DME

Условия реакции

Обработка

1. 1
   Другоеthe reaction medium was degassed
2. 2
   Температураthe mixture was refluxed for 20 hours
3. 3
   ДругоеThe organic phase was separated out
4. 4
   Промывкаwashed with water
5. 5
   Сушкаdried over magnesium sulfate
6. 6
   Другоеevaporated
7. 7
   ДругоеThe residue obtained
8. 8
   Другоеwas purified by chromatography on a column of silica
9. 9
   Промывкаeluted with a mixture of heptane and ethyl acetate (75/25)
10. 10
    ДругоеAfter 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
    Другоеwere collected

Методика

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.

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