Trimethyl borate → 222547-67-3

Temperature

-78 °C

1-fluoro naphthalene (14.61 g, 100 mmol, Aldrich Chemical) was dissolved in dry THF (50 mL) and cooled to -78° C. Then, a sec-butyl lithium solution (1.3 M in hexane, 100 mL) was added to the mixture over a period of 5 minutes. This mixture was stirred for 20 minutes at -78° C., then trimethylborate (15 mL, 132 mmol, Aldrich Chemical) was added. Stirring was continued at -78° C. for 15 minutes followed by stirring at room temperature for 30 minutes. The reaction was quenched by adding 100 mL of a 3:1 mixture of AcOH: H2O and stirred overnight at room temperature. Next, 500 mL of a 1:1 mixture of ethyl acetate and water was added. The organic layer was washed with 10% HCl (200 mL×1), water (200 mL×2), and brine (100 mL), dried over sodium sulfate, filtered, and solvent was removed to yield 18 grams of a white solid. This material was purified by silica-gel chromatography (350 grams of silica gel, ethyl acetate-hexane 1:1 mobile phase) to yield 16.3 g of the title compound (86%).

1. stirringStirring
2. waitwas continued at -78° C. for 15 minutes
3. stirringby stirring at room temperature for 30 minutes
4. customThe reaction was quenched
5. additionby adding
6. addition100 mL of a 3:1 mixture of AcOH
7. stirringH2O and stirred overnight at room temperature
8. additionNext, 500 mL of a 1:1 mixture of ethyl acetate and water
9. additionwas added
10. washThe organic layer was washed with 10% HCl (200 mL×1), water (200 mL×2), and brine (100 mL)
11. dry with materialdried over sodium sulfate
12. filtrationfiltered
13. customsolvent was removed

ORD record

ord-2b041a50bbae467bb55eccde1e28cbf3

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06008379