Cyanogen Bromide → HCID 57457863, compound

Temperature

7.5 °C

In dry ether (100 mL) was dissolved 5.18 g (23.1 mmol) of 1-isopropyl-2-[(2-methoxyethoxy)methoxy]benzene obtained in Example 18(1), 22.3 mL (35.7 mmol) of n-butyl lithium-hexane solution (1.60M) was added dropwise to the solution in an ice bath (reaction solution temperature: 5-10° C.), and the mixture was stirred in an ice bath for 5 hours. To the reaction mixture was added 8.20 g (69.7 mmol) of 90% cyanogen bromide while maintaining the reaction solution temperature to 5-10° C. The reaction mixture was stirred in an ice bath for 2 hours, poured into ice-cold water (300 mL), and extracted with ether. The organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was removed. The residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=100:1) to obtain 3.40 g (11.2 mmol, Yield: 48.5%) of 1-bromo-3-isopropyl-2-[(2-methoxyethoxy)-methoxy]benzene.

1. additionwas added dropwise to the solution in an ice bath
2. custom(reaction solution temperature: 5-10° C.)
3. stirringThe reaction mixture was stirred in an ice bath for 2 hours
4. extractionextracted with ether
5. dry with materialdried over anhydrous sodium sulfate
6. customthe solvent was removed
7. customThe residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=100:1)

ORD record

ord-8f63fe7eabe54661900e70c25c22da02

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07608563B2