1-Bromo-4-iodobenzene → HCID 62906397, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-4-iodobenzene (31.1 g, 110 mmol) in THF (300 ml) (under argon atmosphere) was added isopropylmagnesium chloride (2M in THF) (60 ml, 120 mol) during 10 min at −25° C. The solution was stirred for 1 h at −20° C. and then warmed up to 0° C. and tetrahydro-pyran-4-carbaldehyde (10.98 ml, 100 mmol) was added dropwise over 10 min at 0-7° C. The reaction mixture was quenched with 1M NH4Cl (500 ml) and extracted with EtOAc (2×). The organic phases were washed with water and brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was crystallized from DCM-diisopropyl ether (1:2) to give the title compound as a white solid (24.32 g, 90 mmol, 90%): HPLC: CtRet=4.43 min; 1H-NMR (400 MHz, DMSO-d6): δ 1.07 (d, 1H), 1.21 (m, 2H), 1.62 (m, 2H), 3.15 (m, 2H), 3.78 (m, 2H), 4.23 (m, 1H), 5.26 (d, 1H), 7.35 (dd, 4H)

Provenance & Evidence