Реакция #356749

Уравнение реакции

2-bromophenylboronic acid

4-chloro-2-iodo-1-[(phenylmethyl)oxy]benzene

potassium carbonate

toluene ethanol

2-bromophenylboronic acid

→

colourless gum

Выход 55.1%

2′-Bromo-5-chloro-2-[(phenylmethyl)oxy]biphenyl

Выход 55.1%

Растворители

diethyl ether water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   ТемператураThe mixture was heated for 6 hours
3. 3
   Температураthen cooled
4. 4
   Другоеthe organic phase separated
5. 5
   Сушкаdried (magnesium sulphate)
6. 6
   Другоеevaporated
7. 7
   ДругоеThe residue was purified by chromatography on silica eluting with ethyl acetate/iso-hexane (1:49)
8. 8
   Другоеthen rechromatographed
9. 9
   Промывкаeluting with dichloromethane/iso-hexane (1:9)

Методика

A mixture of 2-bromophenylboronic acid (2.01 g, 10 mmol), 4-chloro-2-iodo-1-[(phenylmethyl)oxy]benzene (3.445 g, 10 mmol), potassium carbonate (5.52 g, 40 mmol) and tetrakis(triphenylphosphine)palladium(0) (580 mg, 0.5 mmol) in 1:1 toluene/ethanol (45 ml) was stirred and heated at 90° C. under nitrogen for 2 hours when a further 1 g (4.98 mmol) of 2-bromophenylboronic acid and 0.2 g (0.17 mmol) of tetrakis(triphenylphosphine)palladium(0) were added. The mixture was heated for 6 hours then cooled, diluted with diethyl ether/water and the organic phase separated, dried (magnesium sulphate) and evaporated. The residue was purified by chromatography on silica eluting with ethyl acetate/iso-hexane (1:49) then rechromatographed eluting with dichloromethane/iso-hexane (1:9) to give 2.06 g of colourless gum which slowly crystallised.

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