Iodine → HCID 22768559, compound

Participants

Reaction Conditions

Reaction Steps

Magnesium turnings (478 g, 19.7 m) in a 12 l, flask were dried as described in Example II. The reactant stock solution was prepared by dissolving 1400 g (9.7m) of para-dichlorobenzene in 3700 g (21m) of di-n-propoxydimethylsilane and 515 g (7.2 m) of tetrahydrofuran. Fresh cuprous chloride (10.0 g, 0.10 m), a crystal of iodine, and 300 ml of the stock solution were added to the magnesium turnings. The vessel was heated to 132° C to initiate the reaction. The remaining stock solution was added over a 3 hour period and the system was refluxed at 137°-144° C for a total of 123/4 hours. The crude product was decanted away from the salt. The salt cake was washed with dry toluene and the washings and crude were combined and flash distilled. A crude product, 2563 g (83.9% yield) was obtained; subsequent fractionation gave 2412 g (79% recovered yield) of 1,4-bis(n-propoxydimethylsilyl)benzene, b.p. 140°-142° C/5 mm vacuum.

Provenance & Evidence