反应详情

温度

0 °C

To a solution of 2-bromo-1,3-dimethoxy-5-(methoxymethyl)benzene (20.0 g, 76.6 mmol) in tetrahydrofuran (200 mL) which had been cooled in a dry ice-acetone bath was added 1.58M n-butyllithium in hexane (50.9 mL, 80.4 mmol) under a nitrogen stream, and the reaction mixture was stirred for 30 minutes. A solution of trimethoxyborane (8.75 g, 84.2 mmol) in tetrahydrofuran (20 mL) was then added to the reaction mixture, and the reaction temperature was increased to 0° C. while stirring. After adding 1N hydrochloric acid (200 mL) to the reaction mixture, it was stirred for 30 minutes at room temperature. After the reaction terminated, toluene (200 mL) was added to the reaction mixture and the organic layer was separated off, after which the aqueous layer was extracted with toluene (100 mL). The combined organic extracts were washed with water (100 mL) and then concentrated under reduced pressure. The residue was dissolved in tert-butyl methyl ether (75 mL) and the reaction mixture was stirred for 30 minutes, after which heptane (223 mL) was added thereto and the reaction mixture was further stirred for 2 hours. The precipitate was filtered out and washed with a mixed solution of tert-butyl methyl ether and heptane (1:3, 3.75 mL), and then dried at 40° C. for 24 hours to afford 12.4 g of the title compound (71.8% yield).

1. stirringwhile stirring
2. stirringwas stirred for 30 minutes at room temperature
3. customAfter the reaction terminated
4. additiontoluene (200 mL) was added to the reaction mixture
5. customthe organic layer was separated off
6. extractionafter which the aqueous layer was extracted with toluene (100 mL)
7. washThe combined organic extracts were washed with water (100 mL)
8. concentrationconcentrated under reduced pressure
9. dissolutionThe residue was dissolved in tert-butyl methyl ether (75 mL)
10. stirringthe reaction mixture was stirred for 30 minutes
11. additionafter which heptane (223 mL) was added
12. stirringthe reaction mixture was further stirred for 2 hours
13. filtrationThe precipitate was filtered out
14. washwashed with a mixed solution of tert-butyl methyl ether and heptane (1:3, 3.75 mL)
15. customdried at 40° C. for 24 hours