Methanol → 9-Decenoxybenzyl bromide

Temperature

0 °C

First, 16.05 g (0.061 M) of 9-decenoxybenzyl alcohol (compound (23)) prepared in Synthetic example 1-2 was dissolved in 85 mL of diethyl ether, and the solution was cooled to 0° C. After cooling, 6.76 g (0.022 M) of phosphorus tribromide (compound (21)) was added dropwise thereto at 5° C. or less. The mixture was aged at 5° C. for 2 hours and then at 15° C. for 1.5 hours. After aging, the solution was cooled to 50° C. Then, 38 mL of methanol was added dropwise at 50° C. or less. After dropwise addition, 73.4 g of a sodium hydrogen carbonate aqueous solution (1 M) was added dropwise at 10° C. or less, and then phase separation was performed. After the separation, the separated organic layer was washed with 32 mL of deionized water and then concentrated. Thereby, 18.19 g of 9-decenoxybenzyl bromide (compound (24)) was produced (yield: 91.6%).

1. temperatureAfter cooling
2. customat 5° C. or less
3. waitat 15° C. for 1.5 hours
4. temperaturethe solution was cooled to 50° C
5. additionwas added dropwise at 10° C. or less
6. customphase separation
7. customAfter the separation
8. washthe separated organic layer was washed with 32 mL of deionized water
9. concentrationconcentrated

ORD record

ord-d209ea33d3bd4db2be251963768b03e8

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07422702B2