and v.p.c. results were corroborated by examining mixtures of known composition of the pure halo aromatics involved.Chemicals.-Practical N-bromosuccinimide (Arapahoe) or purified NBS (Matheson Coleman and Bell) gave equivalent yields of product as did practical or purified N-chlorosuccinimide (Matheson Coleman and Bell) after allowance for inert content.Of the substances used as standards in the v.p.c. or infrared analyses, o-bromochlorobenzene was synthesized by the standard procedure10; all other chemicals were White Label Eastman or reagent grade Matheson Coleman and Bell products whose purity was established by v.p.c. and/or infrared examination.
Communications to the Editor Vol. 7S with the recorded melting point of 220°for 6-chloro-3(2H )benzofurunone semicarbazone.7Proof of Structure of IV by Conversion to 2-Chloro-4methoxybenzoic Acid.-Two grams (0.01 mole) of IV was dissolved in 50 ml. of water containing 2 g. of XaOH and heated to the refluxing temperature. Methyl sulfate (2.ñ g., 0.02 mole) was added slowly and the refluxing continued for 2 hours. At the end of this time, a solution of 8 g. of KMiiO( in 100 ml. of water was added slowly and the refluxing continued for an additional hour. The manganese dioxide was then filtered off with suction, washed with water, and the combined filtrates made strongly acidic with coned. HC1. After cooling overnight in the refrigerator, the light yellow solid was filtered off with suction and recrystallizcd from dilute ethanol to yield 0.8 g. (42%) of short colorless needles, m.p. 204-205°with sublimation. The recorded melting point of 2-chloro-4-methoxybenzoic acid is 208°w ith sublimation.8
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