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POLYHYDROXYALKENES FROM FURFURAL CONDENSATION PRODUCTS 4543 added in several portions, whereupon a clear solution formed. Stirring was continued for 90 minutes at 5°.In the meantime 0.5 g. of sodium sulfite was added to a mixture of 2.0 g. of hydrated copper sulfate, 4.0 g. of sodium bromide, and 1.5 ml. of 1 N sulfuric acid in 10 ml. of water yielding a precipitate of cuprous bromide which was washed repeatedly with water by decantation in a centrifuge tube. This salt, dissolved in 10 ml. of 48% hydrobromic acid, was added to the diazonium solution. The dark mixture was allowed to stand for four hours while coming to room temperature. It was then refluxed for 15 minutes and poured onto cracked ice giving a white precipitate and a brown gum. The mixture was extracted twice with benzene. The benzene solution was washed with water until the washings were neutral, extracted three times with a total of 50 ml. of 1 N potassium hydroxide, and washed again until neutral. Only a small amount of material precipitated upon acidification of the aqueous alkaline solution.The benzene layer was dried over calcium chloride and percolated through an alumina column (1 cm. diameter, 8 cm. high). The column was washed with 20 ml. of benzene and the combined eluates taken to dryness. Methanol (6 ml.) was added to the residue and the mixture was refluxed for five minutes giving a light yellow solution and a mobile brown gum. The solution was decanted through a filter. Crystallization occurred overnight at -10°to give 140 mg. of a mixture of white crystals, m.p. 100-103°, and a tan gum (re-extraction of the brown gum obtained above produced no further crystalline material). Three successive "recrystallizations from 3, 2 and 0.7 ml. of methanol eliminated the gum and yielded 20 mg. of 4-bromofluorene, m.p. 112°.

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