Hydrogen Bromide → HCID 11770285, compound

Temperature

-70 °C

In a 500 ml Schlenk tube (8 cm diameter), 4.5 g (30 mmol) of 2 were dissolved in 150 ml of THF and cooled to -70° C. An aqueous solution of HBr was added dropwise over a period of 5 minutes and the solution was stirred further for 2 hours at this temperature. After removing the cooling bath, the solution thawed to -15° C. over a period of 1.5 hours. The reaction solution was hydrolyzed at this temperature by addition of 40 ml of 10% strength sodium hydroxide solution and was stirred for 1 hour without cooling. During this time, the solution came to room temperature. The aqueous phase was separated off and shaken three times with 30 ml of diethyl ether. The combined organic phases were subsequently washed with saturated sodium chloride solution and dried over sodium sulfate. Removal of the solvent gave a yellow oil. The crude product obtained in this way (6.97 g) can be reacted further without further purification. To characterize the material, part of the crude product was flash-chromatographed on a silica gel column (4*25 cm; eluant: PE/THF in a ratio of 9:1;

1. customAfter removing the cooling bath
2. waitthe solution thawed to -15° C. over a period of 1.5 hours
3. additionThe reaction solution was hydrolyzed at this temperature by addition of 40 ml of 10% strength sodium hydroxide solution
4. stirringwas stirred for 1 hour
5. temperaturewithout cooling
6. customcame to room temperature
7. customThe aqueous phase was separated off
8. stirringshaken three times with 30 ml of diethyl ether
9. washThe combined organic phases were subsequently washed with saturated sodium chloride solution
10. dry with materialdried over sodium sulfate
11. customRemoval of the solvent
12. customgave a yellow oil

ORD record

ord-89cf0226a8224de6be2cd58f0c03e383

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06166234