Benzoyl Peroxide → 2-Bromo-5-(methoxymethyl)-1,3-dimethylbenzene

온도

80 °C

2-bromomesitylene (5.00 g) was dissolved in carbon tetrachloride (50 mL). NBS (4.45 g) and benzoyl peroxide (182 mg) were added to the solution, and the mixture was stirred at 80° C. for three hours. The reaction mixture was returned to room temperature and filtered. The solid collected by filtration was washed with n-heptane. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-heptane). The resulting fraction was concentrated under reduced pressure. The residue was dissolved in THF (120 mL). Sodium methoxide (28% solution in methanol, 9.35 mL) was added to the solution, and the mixture was stirred at 80° C. for four hours. The reaction mixture was returned to room temperature and concentrated under reduced pressure. Water was added to the residue, followed by extraction with DCM. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 5%). The resulting fraction was concentrated under reduced pressure, and the residue was purified again by NH silica gel column chromatography (n-heptane) to give the title compound (880 mg).

1. customwas returned to room temperature
2. filtrationfiltered
3. filtrationThe solid collected by filtration
4. washwas washed with n-heptane
5. concentrationThe filtrate was concentrated under reduced pressure
6. customthe residue was purified by silica gel column chromatography (n-heptane)
7. concentrationThe resulting fraction was concentrated under reduced pressure
8. dissolutionThe residue was dissolved in THF (120 mL)
9. additionSodium methoxide (28% solution in methanol, 9.35 mL) was added to the solution
10. stirringthe mixture was stirred at 80° C. for four hours
11. customwas returned to room temperature
12. concentrationconcentrated under reduced pressure
13. additionWater was added to the residue
14. extractionfollowed by extraction with DCM
15. concentrationThe organic layer was concentrated under reduced pressure
16. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 5%)
17. concentrationThe resulting fraction was concentrated under reduced pressure
18. customthe residue was purified again by NH silica gel column chromatography (n-heptane)

ORD 기록

ord-9012ecba62c0433ab5a891e812fdb66d

출처 데이터셋

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08563565B2