1-Bromo-4-iodobenzene → 8-(4-Bromophenyl)-1,4-dioxa-8-azaspiro[4.5]decane

Participants

Reaction Conditions

Reaction Steps

1,4-Dioxa-8-azaspiro[4.5]decane (1.63 mL) and 1-bromo-4-iodobenzene (3 g) are dissolved in toluene (75 mL), treated with sodium tert-butoxide (1.53 g) and purged for 10 minutes with argon. Acetato-(2′-di-tert.-butylphosphino-1,1′-biphenyl-2-yl)-palladium-(II) (245 mg) is added and the mixture is heated for 15 minutes at 140° C. Then the mixture is partitioned between saturated aqueous NH4Cl solution and ethylacetate. The organic phase is washed with brine and dried (MgSO4). The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30) to give the title compound. LC (method 2): tR=1.06 min; Mass spectrum (ESI+): m/z=298 [M+H]+.

Provenance & Evidence