We report herein a tandem reaction of para-quinone methides with TMSCF 2 Br to construct bromofluoroalkenes in a Zselective manner. While TMSCF 2 Br has been documented as the precursor of difluoro carbene, it exhibits another possibility in this transformation, a formal bromofluoro carbene surrogate. The alkenyl bromide unit of the products could directly engage in a variety of transformations.