Iodine → 1,1'-(Diazomethylene)bis(benzene)

Participants

Reaction Steps

To a solution of benzophenone hydrazone (11.3 g) in CH2Cl2 (58 mL) is added a 1% w/v solution of iodine in CH2Cl2 (2.3 mL) and 1,1,3,3-tetramethylguanidine (7.29 g). 3-Chloroperoxybenzoic acid (11 g) is then added in small portions at room temperature. The solvent is removed in vacuo to provide diphenyl diazomethane. A solution of diphenyl diazomethane (10 g) in EtOAc (22 mL) is then added to a cooled (5° C.) solution of Compound 8 (9.7 g) in THF (170 mL) and EtOAc (170 mL). The mixture is stirred until completion whereupon it is evaporated to dryness in vacuo. THF (73 mL) is added and the insolubles are filtered off. The filtrate is evaporated in vacuo until crystals begin to form. EtOAc (73 mL) is then added and the mixture is stirred for 1.5 hours at 0°-5° C. The resulting solid is filtered to provide Compound 9.

Provenance & Evidence