Sulfuric Acid → HCID 66851757, compound

To a solution of 15.8 g [0.04 mol] of 1-bromo-2-(2′-bromo-2′,2′-dichloroethyl)-5-chloro-3-ethylbenzene in 35 ml of methanol is added dropwise, at 10-20° C., 43 g of a 30% solution of NaOMe in MeOH [0.24 mol]. The mixture is subsequently heated to reflux for 5 hours, then cooled to room temperature, 12.3 g of conc. sulphuric acid are added and the mixture is heated again to reflux for 2 hours. The reaction mixture is cooled to room temperature and then metered in portions into a suspension of 12.7 g of NaHCO3 in 80 ml of water, stirred with 50 ml of methylene chloride and filtered through silica gel, and the filtercake is washed three times with 20 ml each time of methylene chloride. The combined organic phases are extracted by shaking with 20 ml of water and then 20 ml of saturated aqueous NaCl solution, dried over sodium sulphate and concentrated under reduced pressure. This gives 11.55 g of methyl 2-bromo-4-chloro-6-ethylphenylacetate (99% of theory).

1. temperatureThe mixture is subsequently heated
2. temperatureto reflux for 5 hours
3. temperaturethe mixture is heated again
4. temperatureto reflux for 2 hours
5. temperatureThe reaction mixture is cooled to room temperature
6. filtrationfiltered through silica gel
7. washthe filtercake is washed three times with 20 ml each time of methylene chloride
8. extractionThe combined organic phases are extracted
9. dry with material20 ml of saturated aqueous NaCl solution, dried over sodium sulphate
10. concentrationconcentrated under reduced pressure

ORD record

ord-ee553d05a7ce4e55a6866425cd641fe6

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875753B2