HCID 15711866, compound → HCID 54319346, compound

Participants

Reaction Steps

A solution of 0.94 g (3.8 mmol) of 1-cyano-3,4-dihydro-5-hydroxy-3-phenyl-1H-2-benzopyran, the product of Step 3 of Example 89 in 10 mL of glacial acetic acid was treated with a solution of 1.2 g (3.8 mmol) of pyridine hydrobromide perbromide in 50 mL of glacial acetic acid and the resultant mixture was stirred for 48 h at ambient temperature. The precipitate was filtered to afford 351 mg (28% yield) of the title compound. An additional 229 mg (18% yield) of the desired product precipitated from the filtrate after concentration in vacuo, to give a total of 580 mg (46% yield) of [1R,3R] 8-bromo-1-cyano-3,4-dihydro-5-hydroxy-3-phenyl-1H-2-benzopyran.

Provenance & Evidence