Benzyl Bromide → HCID 15631338, compound

Temperature

0 °C

A solution of 0.60 ml (4.2 mmol, 2.2 eq.) of diisopropylamine in 10 ml of dry tetrahydrofuran was cooled to -78° C. and 1.6 ml (3.8 mmol, 2 eq.) of 2.4M n-butyl lithium in hexane was added dropwise. The reaction was warmed to 0° C., stirred for 15 minutes and 0.30 g (1.9 mmol) of 4-methyl-8-quinolinol (see Example 1A) in 10 ml of dry tetrahydrofuran was added. The temperature was maintained at 0° C. for 24 hours, then was cooled to -78° C. and 0.23 ml (1.9 mmol, 1 eq.) of benzyl bromide was added. The reaction was stirred at -78° C. for one hour then stirred at room temperature for one hour. Water was added and this was extracted with ether. The organic layers were washed with saturated ammonium chloride, brine, dried (magnesium sulfate) and concentrated in vacuo. Purification by flash chromatography (silica gel, 1:4 ethyl acetate:petroleum ether) and recrystallization (petroleum ether) gave 240 mg of the title compound as pale green crystals: melting point 102°-103° C.

1. temperatureThe temperature was maintained at 0° C. for 24 hours
2. temperaturewas cooled to -78° C.
3. stirringThe reaction was stirred at -78° C. for one hour
4. stirringthen stirred at room temperature for one hour
5. extractionthis was extracted with ether
6. washThe organic layers were washed with saturated ammonium chloride, brine
7. dry with materialdried (magnesium sulfate)
8. concentrationconcentrated in vacuo
9. customPurification
10. customby flash chromatography (silica gel, 1:4 ethyl acetate:petroleum ether) and recrystallization (petroleum ether)

ORD record

ord-e9a5fb57faa94ca8b0083179962f9b55

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04843082