Trimethyl borate → HCID 89484113, compound

In a flame-dried, 500 mL round bottom flask, 5-(t-butyl)-2,2′-bithiophene (from U152-001, 13 g, 58.5 mmol) was dissolved in anhydrous THF (200 mL) and the solution was cooled to −78° C. (dry ice/acetone). n-butyl lithium (2.5 M in hexanes, 25.7 mL, 64.3 mmol) was added dropwise over a period of 10 minutes, and the resulting green solution was allowed to stir for 15 minutes. Trimethyl borate (19.6 mL, 175 mmol) was added dropwise over a period of 10 minutes, and the resulting light yellow solution was stirred for 2 hours at −78° C., then allowed to warm to room temperature and stirred for 1 hour. The reaction was quenched by pouring it into 10% HCl (500 mL). The organic phase was separated and the aqueous phase extracted with ether (250 mL). The combined organics were washed with water (500 mL), dried over MgSO4, filtered and solvent removed by rotary evaporation. The resulting green solid was dried under vacuum to afford 15 g (96% yield), which was used in the next step without further purification.

1. stirringthe resulting light yellow solution was stirred for 2 hours at −78° C.
2. stirringstirred for 1 hour
3. customThe reaction was quenched
4. additionby pouring it into 10% HCl (500 mL)
5. customThe organic phase was separated
6. extractionthe aqueous phase extracted with ether (250 mL)
7. washThe combined organics were washed with water (500 mL)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customsolvent removed by rotary evaporation
11. customThe resulting green solid was dried under vacuum
12. customto afford 15 g (96% yield), which
13. customwas used in the next step without further purification

ORD record

ord-c4517d6c725b41cb932b647bf5ea07f9

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227986B2