Oxalyl chloride → 5-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

Participants

Reaction Conditions

Reaction Steps

To a benzene solution (60 ml) of 4-(o-bromophenyl) butyric acid (5 g) was added oxalyl chloride (3.6 ml) and the reaction refluxed for 11/2 hrs. The solution was evaporated to dryness, the residue was dissolved in CH2Cl2 (50 ml) then cooled to 0° C., followed by the addition of AlCl3 (3.1 g). The mixture was stirred at 0° C. warming to room temperature overnight. The reaction was poured onto ice, then extracted with CH2Cl2. The organic layer was separated, washed with 1 N NaOH, then brine, separated, dried (MgSO4), filtered and evaporated affording the desired product (4.26 g).

Provenance & Evidence