Ikeuchi, Yutaka; Taguchi, Takeo; Hanzawa, Yuji published the artcile< Zirconocene-Mediated and/or Catalyzed Unprecedented Coupling Reactions of Alkoxymethyl-Substituted Styrene Derivatives>, Safety of Methyl 2-bromo-5-fluorobenzoate, the main research area is alkoxymethylstyrene alkoxy cleavage regioselective stereoselective homodimerization heterodimerization; hydrochrysene stereoselective preparation; aryl hydronaphthalene stereoselective preparation; zirconocene mediated stereoselective cyclization dimerization coupling ortho alkoxymethyl styrene; dependence product zirconocene mediated reaction alkoxymethyl styrene.
2-(Alkoxymethyl)styrenes I (R = H, Me; R1 = H, F, MeO; R2 = Me, PhCH2) undergo a variety of reactions involving cleavage of the alkoxy group with zirconocene generated from zirconocene dichloride and either butyllithium or butylmagnesium chloride. I (R = H) react with stoichiometric amounts of zirconocene to give 4-substituted-2-methylstyrenes or 4-substituted-2-(deuteromethyl)styrenes, while with two equivalent of zirconocene, I (R = R1 = H; R2 = PhCH2) gives 3-ethyl-1-(2-methylphenyl)butane or a trideuterated derivative; in the presence of catalytic zirconocene and 3 equivalent of butylmagnesium chloride, I (R = H; R1 = H, F; R2 = PhCH2) give mainly hexahydrochrysenes II (R = H; R1 = H, F) in 52-57% yields. In the presence of either catalytic or stoichiometric amounts of zirconocene, I (R = Me; R1 = H, F, MeO; R2 = Me, PhCH2) give II (R = Me; R1 = H, F, MeO) in 29-89% yields; with I (R = Me; R1 = F; R2 = Me), the aryltetrahydronaphthalene III {R1 = F; R3 = 2-[(MeO)Me2C]C6H4} is obtained in the presence of stoichiometric zirconocene in 28-50% yields as a single stereoisomer. I (R = Me; R1 = H; R2 = Me) couples with excess amounts of arylethylenes R3CH:CH2 [R3 = Ph, 4-FC6H4, 3,5-(F3C)2C6H3, 4-MeOC6H4, 2-MeOC6H4] in the presence of stoichiometric zirconocene to yield aryldihydronaphthalenes III [R1 = H; R3 = Ph, 4-FC6H4, 3,5-(F3C)2C6H3, 4-MeOC6H4, 2-MeOC6H4] in 11-85% yields (as single stereoisomers) in addition to 5-60% yields of II (R = Me; R1 = H).
Journal of Organic Chemistry published new progress about Aryl alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 6942-39-8 belongs to class bromides-buliding-blocks, and the molecular formula is C8H6BrFO2, Safety of Methyl 2-bromo-5-fluorobenzoate.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary