[C:1](=[O:4])([O-])[O-].[K+].[K+].[SH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Br[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.Cl>CN(C)C=O>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([S:7][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([S:7][C:8]4[CH:13]=[CH:12][C:1]([OH:4])=[CH:10][CH:9]=4)=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[CH:9][CH:10]=1Potassium carbonate (75.9 g, 0.55 mol) was charged to a 2 liter flask equipped with a stirrer, condenser, dropping funnel, thermometer and nitrogen purge. Dimethylformamide (200 ml) was added and the solution heated to 80°-90° C. 4-mercaptophenol (69.3 g, 0.55 mol) in 200 ml of dimethylformamide was added to the stirred reaction mixture over one hour. The reaction mixture was maintained at 100°-110° C. for two hours. Solid 4,4'-dibromobiphenyl (78 g, 0.25 mol) was then added over one hour. The reaction mixture was refluxed for 18 hours, cooled to room temperature, and poured into 10% HCl. The white to yellow solid was collected with suction and washed with water. The solid was treated with 5-10% NaOH and filtered once more with suction. The mother liquor was acidified to pH≈2 and the solid collected and recyrstallized from chlorobenzene/methanol. A 34% yield of pure HPSB was obtained having a melting point of 214°-217° C.
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