Diazald → 5-Chloro-2,3-dihydro-1-benzofuran-3-one

Participants

Reaction Steps

According to the procedure of M. E. Jung et al., J. Org. Chem., 53, 423 (1988), a solution of diazomethane in ether [prepared from N-methyl-N-nitroso-p-toluenesulfonamide (5.8 g, 0.026 mol) and potassium hydroxide (2.9 g, 0.052 mol) in H2O (7 mL), ethanol (10 mL), and ether (70 mL) utilizing a mini-Diazald® apparatus] was added to 5-chloro-2-methoxybenzoyl chloride (2.0 g, 0.010 mol). The resulting mixture was stirred for 30 minutes, concentrated, and acetic acid (20 mL) was added. After 15 minutes, the mixture was concentrated to give 1.6 g (97%) of the product as an orange solid.

Provenance & Evidence