Hydrochloric Acid → 2-(Methoxymethoxy)-3-methylphenylboronic acid

Temperature

0 °C

To a solution of 1-(methoxymethoxy)-2-methylbenzene in diethyl ether (0.3M) cooled at −60° C. tBuLi in pentane (1.7M, 1.4 eq) was added dropwise and the mixture was stirred for 1 h while warming gradually to 0° C. then for further 2 h at 0° C. The mixture was cooled to −78° C. and a solution of B(OMe)3 in THF (3 eq, 3.0M) was added dropwise and the mixture was allowed to reach RT and stirred overnight. The mixture was cooled to 0° C. and 1N HCl was added, then the reaction mixture was stirred for 2 h. All volatiles were removed under reduced pressure and the residue was extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over Na2SO4, filtered and evaporated in vacuo to give a yellow solid which was triturated with PE to give a white solid which was used in the next step without further purification.

1. additionwas added dropwise
2. waitfor further 2 h at 0° C
3. temperatureThe mixture was cooled to −78° C.
4. customto reach RT
5. stirringstirred overnight
6. temperatureThe mixture was cooled to 0° C.
7. stirringthe reaction mixture was stirred for 2 h
8. customAll volatiles were removed under reduced pressure
9. extractionthe residue was extracted with EtOAc
10. washThe combined extracts were washed with H2O and brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. customevaporated in vacuo
14. customto give a yellow solid which
15. customwas triturated with PE
16. customto give a white solid which
17. customwas used in the next step without further purification

ORD record

ord-11eb261c0b2343a8959ceb669e960d77

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989438B2