Water → (+/-)-2,6-Dichloro-alpha-methyl4-nitrobenzeneacetonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromodihydro-2(3H)-furanone (0.0081 mole) in DMF (16 ml) was added dropwise at room temperature to a mixture of intermediate (10)(0.00773 mole) and NaHCO3 (0.0081 mole) in DMF (30 ml). The mixture was stirred at 70° C. for 5 hours and brought to room temperature. H2O and a saturated NaCl solution were added. The mixture was extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15-40 μm). The pure fractions were collected and the solvent was evaporated. The residue was taken up in DIPE. The precipitate was filtered off and dried, yielding 1.24 g of compound 1 having a melting point of 72° C. and represented by the formula

Provenance & Evidence