Triisopropyl borate → HCID 57582338, compound

Temperature

-70 °C

To a stirred solution of the 2-bromo-4-ethoxy-1-trifluoromethoxy-benzene (Preparation 85, 884 mg, 3.10 mmol) in anhydrous tetrahydrofuran (10 ml) was added n butyl lithium (2M solution in cyclohexanes, 2.33 ml, 4.65 mmol) while maintaining the temperature below −70° C. under an atmosphere of nitrogen. The solution was stirred at this temperature for 1 hour then tri-isopropylborate (875 mg, 4.65 mmol) was added, and the reaction maintained at −70° C. for a further 2 hours. The reaction mixture was then quenched by the addition of ammonium chloride (aqueous solution) (5 ml), followed by acidification with hydrochloric acid (2N aqueous solution) (10 ml). The layers were separated and the organic layer was dried over anhydrous MgSO4 (s), filtered and evaporated in vacuo to afford crude title compound as a white solid (552 mg, 71%). Material was taken on without further purification.

1. temperaturewhile maintaining the temperature below −70° C. under an atmosphere of nitrogen
2. customThe reaction mixture was then quenched by the addition of ammonium chloride (aqueous solution) (5 ml)
3. customThe layers were separated
4. dry with materialthe organic layer was dried over anhydrous MgSO4 (s)
5. filtrationfiltered
6. customevaporated in vacuo

ORD record

ord-36ab218ae1804c98ad7f16ed775884dc

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08134007B2