Triethyl borate → 4-Benzyloxy-5-ethyl-2-methoxy-phenylboronic acid

Under a nitrogen atmosphere, 16.70 g (52.00 mmol) of 5-benzyloxy-2-bromo-4-ethyl-1-methoxybenzene (4) was added to 110 mL of anhydrous THF. The solution was cooled to −78° C., and 22.88 mL (57.19 mmol) of a 2.5 M solution of butyl lithium was added dropwise while maintaining the temperature below −70° C. The reaction mixture was stirred at −78° C. for 45 minutes. 9.73 mL (57.19 mmol) of triethyl borate was then added, and the reaction was allowed to stir at −78° C. for an additional 2 hours. The reaction mixture was then allowed to warm to 23° C. over a 30 minute period and was quenched with 100 mL of saturated NH4Cl. The pH was adjusted to 5.0 with 1M HCl, and the resultant solution was extracted with ethyl acetate (2×200 mL). The combined extracts were washed with brine (1×100 mL), dried over sodium sulfate, filtered and concentrated in vacuo to yield crude product as a greenish-tan solid. The crude product was triturated with hexane and filtered to afford 10.65 g (64%) of 4-benzyloxy-5-ethyl-2-methoxy-phenylboronic acid (5) as an off-white solid.

1. temperaturewhile maintaining the temperature below −70° C
2. stirringto stir at −78° C. for an additional 2 hours
3. temperatureto warm to 23° C. over a 30 minute period
4. customwas quenched with 100 mL of saturated NH4Cl
5. extractionthe resultant solution was extracted with ethyl acetate (2×200 mL)
6. washThe combined extracts were washed with brine (1×100 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto yield crude product as a greenish-tan solid
11. customThe crude product was triturated with hexane
12. filtrationfiltered

ORD record

ord-71d6b7339a874869ab55ecf5912af0a3

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06803470B2