Diiodomethane → 5'-Bromo-2',3'-dihydrospiro[cyclopropane-1,1'-indene]

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Reaction Steps

The title compound was synthesized in analogy to example S87 using diethyl zinc (3.25 ml, 1M solution in hexane, 3.25 mmol), trifluoroacetic acid (251 μl, 3.25 mmol), CH2I2 (262 μl, 3.25 mmol) and 5-bromo-1-methyleneindan (340 mg, 1.63 mmol). The isolated residue was purified by flash column chromatography (100% pentane) to give 5′-bromo-2′,3′dihydro-spiro[cyclopropane1,1′-[1H]indene](345 mg, 95%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.40-7.29 (m, 3H), 3.02 (apt t, J=7.5 Hz, 2H), 2.11 (apt t, J=7.5 Hz, 2H), 0.96-0.84 (m, 4H).

Provenance & Evidence