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4-Bromoanisole finds application as an intermediate in synthetic chemistry. It is used in the preparation of aryl 1,3-diketones and ethyl 4-methoxycinnamate. It is a used as a brominating reagent. Further, it is used in Suzuki coupling reaction with phenylboronic acid as well as in Heck reaction.
Nucleophilic displacement of Br can be effected with Na alkoxides in NMP in the presence of CuBr: Tetrahedron, 48, 3633 (1992).
For formation of the Grignard, conversion to the stannane and Stille coupling with an aryl triflate, catalyzed by trans-Dichlorobis(triphenylphosphine)palladium(II), 10491, see: Org. Synth. Coll., 9, 553 (1998).
Moore, J. N.; Laskay, N. M.; Duque, K. S.; Kelley, S. P.; Rogers, R. D.; Shaughnessy, K. H. Synthesis of 4-sulfonatobenzylphosphines and their application in aqueous-phase palladium-catalyzed cross-coupling. J. Organomet. Chem. 2015, 777, 16-24.
Semmes, J. G.; Bevans, S. L.; Mullins, C. H.; Shaughnessy, K. H. Arylation of diethyl malonate and ethyl cyanoacetate catalyzed by palladium/di-tert-butylneopentylphosphine. Tetrahedron Lett. 2015, 56 (23), 3447-3450.
Gefahrenhinweise (EU): H303
May be harmful if swallowed.
Call a POISON CENTER/doctor if you feel unwell.