Hydrochloric Acid → HCID 66961506, compound

Temperature

-78 °C

4-Bromophenylacetic acid (1.00 g, 4.65 mmol) was dissolved in 45 mls of dry THF and chilled to −78° C. To this was added LDA (9.30 mls, 18.6 mmol, 2M in THF/heptane), resulting in a dark color, and this mixture was stirred at −78° C. for 20 minutes. (2-bromoethoxy)(tert-butyl)dimethylsilane (1.20 mls, 5.58 mmol) was then added via syringe, and then the cooling bath was removed to allowed the reaction to warm to room temperature. Upon warming, the mixture became an amber color. Once at room temperature, 50 mls of 1N aqueous HCl were then added and the mixture was vigorously stirred for 16 hours, then extracted with EtOAc (2×), extracts washed with 2M aqueous sodium carbonate, dried over sodium sulfate and concentrated to an orange oil. Flash 40 Biotage (40M cartridge, 3:1 Hexane:EtOAc) afforded 211 mgs (19%) of 3-(4-bromophenyl)dihydrofuran-2(3H)-one as an orange oil.

1. customresulting in a dark color
2. customthe cooling bath was removed
3. customthe reaction
4. temperatureto warm to room temperature
5. temperatureUpon warming
6. stirringthe mixture was vigorously stirred for 16 hours
7. extractionextracted with EtOAc (2×)
8. washextracts washed with 2M aqueous sodium carbonate
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated to an orange oil

ORD record

ord-3b173f1b1b324f9b8c1b8bb821f54fc6

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691809B2