Trimethyl borate → 2-Dimethylamino-6-methoxyphenylboronic acid

To a solution of 5.3 g (35 mmol) of 3-dimethylamino-anisole in 25 mL of dry THF at −78° C. was added 19 mL (47 mmol) of a 2.5M solution of n-butyl lithium in hexanes. The reaction mixture was stirred for 1 hour before removing the ice bath and warming to room temperature for 90 minutes. The solution was cooled to −78° C., treated with 8.75 g (84 mmol) of trimethyl orthoborate, and then stirred for one hour before warming to room temperature for one hour. The reaction was quenched by the addition of 20 mL of water and sufficient acetic acid to neutralize the mixture. The reaction mixture was extracted with ethyl acetate (3×30 mL), and the combined organic extracts were extracted with 1N NaOH solution (4×15 mL). The combined aqueous extracts were acidified with acetic acid and extracted with EtOAc (3×20 mL). The organic phase was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 2-methoxy-6-dimethylamino-phenylboronic acid.

1. custombefore removing the ice bath
2. temperatureThe solution was cooled to −78° C.
3. stirringstirred for one hour
4. temperaturebefore warming to room temperature for one hour
5. customThe reaction was quenched by the addition of 20 mL of water and sufficient acetic acid
6. extractionThe reaction mixture was extracted with ethyl acetate (3×30 mL)
7. extractionthe combined organic extracts were extracted with 1N NaOH solution (4×15 mL)
8. extractionextracted with EtOAc (3×20 mL)
9. washThe organic phase was washed with brine
10. dry with materialdried over anhydrous MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORDレコード

ord-6d6ba40121be444d8ee27cbbcb92c9ad

出典データセット

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06403584B1