Реакция #46715

Уравнение реакции

4-(4-bromo-benzyloxy)-2-hydroxy-benzoic acid

3-acetylbenzene boronic acid

Na2CO3

→

4-(3′-Acetyl-biphenyl-4-ylmethoxy)-2-hydroxy-benzoic acid

Растворители

dimethoxymethane

H2O

Условия реакции

Обработка

1. 1
   ДругоеThe solution was flushed with argon, Cl2Pd(PPh3)2 (˜2.5 mol %)
2. 2
   workup.ADDITIONwas added
3. 3
   ФильтрацияThe resulting black solution was filtered (Gelman Acrodisc GHP, Ø25 mm)
4. 4
   workup.ADDITIONslowly added to a cold 1 M HCl (aq.; 15 mL) solution
5. 5
   ФильтрацияThe precipitate was filtered off
6. 6
   Промывкаthoroughly washed with water
7. 7
   ДругоеDrying in vacuo
8. 8
   Другоеyielded 195 mg (88%) of a greyish, solid compound with satisfactorily purity

Методика

A mixture of 4-(4-bromo-benzyloxy)-2-hydroxy-benzoic acid (196.3 mg; 0.6075 mmol), 3-acetylbenzene boronic acid (99.7 mg; 0.6080 mmol) and Na2CO3 (−4 eq.) was dissolved in dimethoxymethane (4 mL) and H2O (2 mL). The solution was flushed with argon, Cl2Pd(PPh3)2 (˜2.5 mol %) was added and the mixture stirred under an atmosphere of argon at 100° C. for 16 hours. The resulting black solution was filtered (Gelman Acrodisc GHP, Ø25 mm) and slowly added to a cold 1 M HCl (aq.; 15 mL) solution. The precipitate was filtered off and thoroughly washed with water. Drying in vacuo yielded 195 mg (88%) of a greyish, solid compound with satisfactorily purity. Mp. 215-220° C. (decomposes); MS (ESI−): 361 (MH−)

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