4-Bromoanisole → HCID 18675130, compound

Reaction equation

Br[CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[O:3]1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[C:18]([CH:2]2[C:7](=[O:8])[NH:6][C:5]3[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=3[O:3]2)[CH:19]=1

Participants

Procedure

To 2-bromo-2H-1,4-benzoxazin-3(4H)-one (I10) (1.40 g, 6.14 mmoles) in methylene chloride (20 mL) was added 4-bromoanisole and then tin (IV) chloride. Addition of tin (IV) chloride caused a brown solution to form. The solution was refluxed for 5 hours, diluted with methylene chloride (100 mL) and washed with water (2×50 mL). After drying over Magnesium sulphate the mixture was concentrated until the product (I11) precipitated (0.58 g). Concentration of the mother liquors and chromatography on silica gel afforded an additional amount of product (I11) (0.55 g).