Hydrochloric Acid → (3-(Methoxymethoxy)phenyl)boronic acid

Temperature

-78 °C

10 g (57.8 mmol) of 3-bromophenol are dissolved in 150 mL of anhydrous DMF. 2.55 g (63.6 mmol) of 60% sodium hydride are then added and the reaction medium is stirred for 1 hour. 4.83 mL (63.6 mmol) of methoxymethyl chloride are then added dropwise and the reaction mixture is stirred for 1 h. After treatment with saturated ammonium chloride solution, extraction with ethyl ether and evaporation of the solvents from the organic phase, the residue obtained is dissolved in 200 mL of anhydrous THF. The mixture is cooled to −78° C. and 25.4 mL (63.6 mmol) of 2.5M butyllithium solution are then added. After stirring for 1 hour at −78° C, 15 mL (65 mmol) of triisopropyl borate are added dropwise. The reaction medium is stirred for 1 hour and then warmed to room temperature, after which it is treated with 1N hydrochloric acid solution. The medium is then extracted with ethyl acetate, after which the organic phases are combined, dried and then concentrated under reduced pressure. After slurrying in heptane and then concentration, a brown solid is obtained (m.p.=45° C., m=5.8 g; Y=67%).

1. stirringthe reaction mixture is stirred for 1 h
2. extractionAfter treatment with saturated ammonium chloride solution, extraction
3. customwith ethyl ether and evaporation of the solvents from the organic phase
4. customthe residue obtained
5. stirringAfter stirring for 1 hour at −78° C
6. stirringThe reaction medium is stirred for 1 hour
7. temperaturewarmed to room temperature
8. extractionThe medium is then extracted with ethyl acetate
9. customdried
10. concentrationconcentrated under reduced pressure
11. concentrationconcentration
12. customa brown solid is obtained (m.p.=45° C., m=5.8 g; Y=67%)

ORD record

ord-2a1878b61ce64b768ebcd2649e3b77cb

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06831106B1