Pyridine → HCID 20405953, compound

Participants

Reaction Conditions

Reaction Steps

The t-butyl octahydro-1H-isoindole-1-carboxylate hydrochloride is prepared as follows. Following a procedure given in Gazz. Chim. Ital, 106, 65(1976), 56 g of (2-methylphenyl)acetyl chloride is converted to 2-bromo-(2-bromomethylphenyl)acetyl chloride. This is added dropwise to a solution of 78.6 g of t-butyl alcohol in 120 ml of ether and cooled at 0° C. Finally 26.4 g of pyridine is added. After a few minutes, the precipitated solids are filtered and washed with ether. The filtrate is washed successively with water and dilute sodium bicarbonate solution dried and concentrated at reduced pressure. t-Butyl 2-bromo-(2-bromomethylphenyl)acetate is obtained as an oil of sufficient purity for further use by chromatography over silica gel, eluting with a 4:1 hexane/ethyl acetate mixture.

Provenance & Evidence