Hydrochloric Acid → 3-Methoxymethoxy-2-methylbenzene-1-boronic acid

HRID 2307554Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][O:10][CH3:11])[C:3]=1[CH3:12].C([Li])CCC.[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C.Cl>C1COCC1>[CH3:11][O:10][CH2:9][O:8][C:4]1[C:3]([CH3:12])=[C:2]([B:18]([OH:23])[OH:19])[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: -78 °C

Procedure

16.2 g (70 mmol) of 1-bromo-3-methoxymethoxy-2-methylbenzene are dissolved in 200 mL of anhydrous THF and the mixture is cooled to −78° C. 33.7 mL (84 mmol) of 2.5M butyllithium are added slowly and the mixture is then maintained at −78° C. for 1 hour. 19.4 mL (84 mmol) of triisopropyl borate are then added dropwise over a period of 15 minutes. The medium is stirred for 30 minutes at the same temperature and then poured into 300 mL of 1N hydrochloric acid. After the usual treatment, the whitish solid residue obtained is rinsed with heptane and then dried under reduced pressure. A flaky white solid is obtained (m=11.8 g; Y=86%).

Workup

temperaturethe mixture is then maintained at −78° C. for 1 hour
customAfter the usual treatment, the whitish solid residue obtained
washis rinsed with heptane
customdried under reduced pressure
customA flaky white solid is obtained (m=11.8 g; Y=86%)

Sources & evidence

ORD record: ord-fff9815d4a8f4b73b381e9200de5e50b
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831106B1

Reaction notes

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