The　synthesis　of　3-tert-butyl-2-hydroxy-5-(pyridin-4-yl)benzaldehyde　by　Suzuki　cross　coupling　reaction　of　5-bromo-3-tert-butyl-2-hydroxybenzaldehyde　with　pyridin-4-ylboronic　acid　was　studied　by　using　different　catalysts　[Pd(dppf)2Cl2,　Pd(OAc)2　and　Pd(PPh3)4],　bases　(Na2CO3,　NaHCO3,　K2CO3,　K3PO4,　Cs2CO3　and　CsF)　and　solvents　(DME/H2O,　DMF/H2O　and　dioxane/H2O)　under　different　temperature　of　70,　80　and　100℃.　A　compatible　method　was　developed　for　the　coupling　reaction　of　arylboronic　acids　(having　electron　donating　or　withdrawing　group)　with　aryl　bromides　(having　electron　withdrawing　group).　Under　the　condition　of　Pd(PPh3)4,　K2CO3,　dioxane/H2O　(V:V=4:1),　80℃,　the　yield　is　excellent　(97%)　and　the　product　separation　is　easy.　The　compatibility　for　aryl　bromides　with　electron　donating　group　is　moderate.　©　2014　Chinese　Chemical　Society　&　SIOC,　CAS