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1-Bromo-2-fluorobenzene is used as a reactant with cyclopenta-1,3-diene to produce 1,4-dihydro-1,4-methano-naphthalene. This reaction will need reagent Mg, and solvent diethyl ether. The reaction time is 3 hours with the temperature of 20°C,
KG Rutherford.; W Redmond. 1-Bromo-2-Fluorobenzene. Organic Syntheses. 1963, 100, (1), 54-62.
M Feuerstein.; H Doucet.; M Santelli. Tetraphosphine/palladium-catalysed Suzuki cross-coupling with sterically hindered aryl bromides and arylboronic acids. Tetrahedron Letters. 2001, 42, (38), 6667-6670.
On treatment with Mg: J. Org. Chem., 49, 4518 (1984), or n-BuLi: Tetrahedron, 48, 4379 (1992), benzyne is generated, which undergoes [4+2] cycloadditions with furans or pyrroles.
Whereas n-BuLi effects bromine-metal exchange, lithiation with LDA at -75o results in deprotonation ortho to F; subsequent reaction with electrophiles provides access to mixed dihalo derivatives such as 3-bromo-2-fluorobenzoic acid: Tetrahedron Lett., 36, 881 (1995). Improved yields are obtained by the use of lithium 2,2,6,6-tetramethylpiperidide (LTMP) as base: Tetrahedron Lett., 37, 6551 (1996).
Hazard Statements: H226-H302-H319
Flammable liquid and vapour. Harmful if swallowed. Causes serious eye irritation.
Precautionary Statements: P280f-P305+P351+P338
Wear protective clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.