4-Bromoanisole → HCID 18675130, compound

HRID 1635045Notes

Reaction equation

HRID 1635045 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

5

Reactant 3

HCID 77304-BromoanisoleHCID 24287Tin tetrachloride2×HCID 18675343139115-80-3

Product 1

HCID 18675130HCID 18675130, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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).

Workup

  1. customto form
  2. temperatureThe solution was refluxed for 5 hours
  3. washwashed with water (2×50 mL)
  4. dry with materialAfter drying over Magnesium sulphate the mixture
  5. concentrationwas concentrated until the product (I11)
  6. customprecipitated (0.58 g)
  7. customConcentration of the mother liquors and chromatography on silica gel afforded an additional amount of product (I11) (0.55 g)

Sources & evidence

ORD record
ord-bdd861e6d9ee4df0bb98c360d37d65bd
Source dataset
uspto-grants-2003_01
Patent number
US06509335B1

Reaction notes

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