Water → 2-(5-Bromo-2-trifluoromethoxyphenyl)cyclopentane-1,3-dione

To a solution of 5-bromo-2-trifluoromethoxybenzaldehyde (2.0 g, 7.43 mmol) in anhydrous dichloromethane (40 ml) at room temperature is added boron trifluoride etherate (1.13 ml, 8.92 mmol) then 1,2-bis(trimethylsiloxy)cyclobutene (2.86 ml, 11.2 mmol). The mixture is stirred at room temperature for 23 hours, followed by addition of distilled water (1.2 ml) and additional boron trifluoride etherate (14.1 ml, 112 mmol). After stirring for 24 hours at room temperature the reaction mixture is then quenched with saturated aqueous ammonium chloride solution (50 ml) and extracted with dichloromethane (2×50 ml). The crude product is extracted from the organic phase by washing with 0.5 M aqueous potassium carbonate solution (×3), then acidified to pH 1 with concentrated hydrochloric acid. Final extraction with dichloromethane (×3) is followed by washing with brine then drying over magnesium sulfate and filtration. Concentration in vacuo gives a crude product which is purified by preparative reverse phase HPLC to afford 2-(5-bromo-2-trifluoromethoxyphenyl)cyclopentane-1,3-dione.

1. stirringAfter stirring for 24 hours at room temperature the reaction mixture
2. customis then quenched with saturated aqueous ammonium chloride solution (50 ml)
3. extractionextracted with dichloromethane (2×50 ml)
4. extractionThe crude product is extracted from the organic phase
5. washby washing with 0.5 M aqueous potassium carbonate solution (×3)
6. extractionFinal extraction with dichloromethane (×3)
7. washby washing with brine
8. dry with materialthen drying over magnesium sulfate and filtration
9. concentrationConcentration in vacuo
10. customgives a crude product which
11. customis purified by preparative reverse phase HPLC

ORDレコード

ord-1793309170154391a4d744f66aa7275b

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08530388B2