Octanoyl chloride → Bromoxynil octanoate

Participants

Reaction Steps

To a 1 L flask fitted with a condenser, mechanical stirrer, condenser, gas inlet port, and a sodium hydroxide scrubber was charged 4-hydroxybenzonitrile (62.5 g, 525 mmol), calcium bromide monohydrate (125.9 g, 577 mmol), and water (350 mls). To the resulting suspension was slowly added a 46% w/w sodium hydroxide solution (160 g, 1838 mmol) such that the temperature did not rise above 30° C. Chlorine gas (85 g, 1197 mmol) was bubbled into the suspension at such a rate that the temperature did not rise above 50° C. and that the bromine fumes were not visible. When the chlorine addition was complete, the suspension was stirred for one hour. To the suspension was charged toluene (300 mls), and octanoyl chloride (89.6 g, 551 mmol) was then added to the rapidly-stirred solution over half an hour, while the temperature was kept below 30° C. When addition was complete, stirring was continued for an hour. Stirring was stopped, the phases were separated and the toluene layer was washed with 15% brine solution (200 mls). The toluene layer was dried by azeotropic distillation of water to give 330 g of a brick red solution of bromoxynil octanoate.

Provenance & Evidence