3-Hydroxybenzaldehyde → 3-(2-Bromoethoxy)benzaldehyde

A mixture of 3-hydroxybenzaldehyde (5.17 g, 42.33 mmol), K2CO3 (58.5 g) and CH3CN (100 ml) was stirred at room temperature for 15 minutes, then dibromoethane (18.3 ml) was added. The reaction mixture was stirred at room temperature for 30 minutes, then at reflux for 3-4 hours. Additional dibromoethane was added and then the reaction mixture was refluxed overnight. The reaction mixture was cooled, filtered, and the filtrate was stripped to afford an oil. The oil was dissolved in ether (300 ml), washed with 5N NaOH (2×75 ml) and the ether layer was dried over MgSO4 and stripped. The residue was purified by column chromatography on silica gel eluting with 10% ethyl acetate/hexane to afford 5.23 g of 3-(2-bromoethoxy)benzaldehyde.

1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
2. temperatureat reflux for 3-4 hours
3. temperaturethe reaction mixture was refluxed overnight
4. temperatureThe reaction mixture was cooled
5. filtrationfiltered
6. customto afford an oil
7. washwashed with 5N NaOH (2×75 ml)
8. dry with materialthe ether layer was dried over MgSO4
9. customThe residue was purified by column chromatography on silica gel eluting with 10% ethyl acetate/hexane

ORD record

ord-906f685a24c447c887bf4cd3a385dd1f

Source dataset

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05958929