Water → HCID 86703828, compound

Temperature

0 °C

At 0° C., to a stirred solution of 4-(5-bromo-2-chlorobenzyl)phenol (6.85 g, 23 mmol) in dimethylformamide (100 mL) was added portionswise sodium hydride (60% in mineral oil, 1.01 g, 25.3 mmol), the mixture was stirred at 0° C. for further 30 minutes. Chloromethyl ether (2.02 g, 25.3 mmol) was slowly added in drops and when the addition finished, the mixture was stirred at room temperature for further 3 hours. Water (150 mL) was added, the mixture was extracted for two times with ethyl acetate, the combined organic phases were washed with saturated brine for one time and dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 20:1) to afford the target compound.

1. additionthe addition
2. stirringthe mixture was stirred at room temperature for further 3 hours
3. extractionthe mixture was extracted for two times with ethyl acetate
4. washthe combined organic phases were washed with saturated brine for one time
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was evaporated under vacuum
7. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 20:1)
8. customto afford the target compound

ORD record

ord-c3fb234b2482475b8015b831633d04fa

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980829B2