[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:4][C:5]2[N:9]=[N:8][NH:7][C:6]=2[CH:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:32]1[CH:37]=[CH:36][CH2:35][CH2:34][CH2:33]1>C(Cl)(Cl)Cl.ClCCl>[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:4][C:5]2[N:9]=[N:8][N:7]([CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][O:32]3)[C:6]=2[CH:10]=1A solution of 6-bromo-5-(2,4-difluorophenoxy)-1H-1,2,3-benzotriazole (0.047 g, 0.14 mmol) and p-toluenesulfonic acid monohydrate (0.0027 g, 0.014 mmol) in chloroform (0.65 mL) was treated with dihydropyran (0.0197 mL, 0.216 mmol) and stirred at 60° C. for 1 h. The reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate. The aqueous layer was separated and re-extracted with dichloromethane. The combined organic layers were separated, washed with water and brine, dried with magnesium sulfate, filtered, and concentrated to a crude oil. Purification by flash column chromatography (100% hexanes to 60% EtOAc/hexanes) gave the desired product as a mixture of isomers that was used without further purification.
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