Iodine → HCID 10172919, compound

Participants

Reaction Steps

A Grignard solution was prepared from p-fluorobromobenzene (197.6 g) and magnesium turnings (28.15 g) in tetrahydrofuran (1250 ml), in the presence of 1,2-dibromoethane and iodine. The Grignard solution was added to a suspension in tetrahydrofuran (1050 ml) of 5-bromophthalide (150 g) and magnesium bromide, prepared in situ from magnesium and 1,2-dibromoethane over a period of two hours at a temperature below 20° C. After addition was complete, the mixture was stirred, and a Grignard solution of N,N-dimethylaminopropylmagnesium chloride was added to the solution over a period of time at a temperature below 20° C. for more than one hour. The result was mixture was poured into saturated ammonium chloride solution (4500 ml) over a period of time at a temperature below 30° C.

Provenance & Evidence