Triisopropyl borate → 4-Methoxy-3-(1-methylethyl)phenylboronic acid

Temperature

-78 °C

To a cooled (−78° C.), stirred solution of 3-isopropyl-4-methoxybromobenzene (2.5 g) was added n-butyllithium (4.8 mL of a 2.5 M solution in hexanes) dropwise. After 30 min, triisopropylborate (5 mL) was added and the reaction solution was allowed to warm to RT and then stirred for 18 h. The reaction solution was concentrated in vacuo, saturated aqueous sodium bicarbonate was added and the resulting mixture was stirred for 30 min. The reaction was extracted with ethyl acetate. The organic layer was washed with water then brine, dried over sodium sulfate, and concentrated in vacuo to afford a solid, which was triturated with hexanes to afford the title compound as colorless plates (1.1 g).

1. temperatureto warm to RT
2. concentrationThe reaction solution was concentrated in vacuo, saturated aqueous sodium bicarbonate
3. additionwas added
4. stirringthe resulting mixture was stirred for 30 min
5. extractionThe reaction was extracted with ethyl acetate
6. washThe organic layer was washed with water
7. dry with materialbrine, dried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customto afford a solid, which
10. customwas triturated with hexanes

ORD record

ord-85d4ba9bb2f74594bf4353388746921d

Source dataset

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06194454B1