Phenyltrimethylammonium bromide dibromide → HCID 22473920, compound

Temperature

0 °C

Phenyltrimethylammonium tribromide (1.58 g) was added in portions under nitrogen at 0° C. over 30 minutes to a stirred solution of 1-(4,5-dichlorobenzo[b]thiophen-2-yl)propan-1-one (1.09 g) in tetrahydrofuran (80 ml), then the mixture was stirred at 0° C. for 30 minutes, at ambient temperature for 18 hours and at reflux temperature for 5 hours. Further phenyltrimethylammonium tribromide (0.79 g) was added, the mixture was heated under reflux for 2 hours, then it was cooled to ambient temperature and filtered. The solvent was removed in vacuo to give a brown oil which was purified by flash chromatography over silica using a 3:1 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 2-bromo-1-(4,5-dichlorobenzo[b]thiophen-2-yl)propan-1-one (1.59 g) as an oil which was used without further purification.

1. temperatureat reflux temperature for 5 hours
2. temperaturethe mixture was heated
3. temperatureunder reflux for 2 hours
4. temperatureit was cooled to ambient temperature
5. filtrationfiltered
6. customThe solvent was removed in vacuo
7. customto give a brown oil which
8. customwas purified by flash chromatography over silica using
9. additiona 3:1 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane as eluant
10. customthe solvents removed in vacuo

ORD record

ord-d2c20d4bce764e53bcccb78baff42640

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06900216B2