Hydrochloric Acid → 3-Benzyloxy-phenylboronic acid

HRID 1455899Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH:16]([OH:18])[OH:17].C([Li])CCC.B(OC(C)C)(OC(C)C)OC(C)C.Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([B:16]([OH:18])[OH:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

The 3-benzyloxybromobenzene of formula IV is converted to the boronic acid derivative by dissolving in THF and adding one equivalent of n-butyllithium at -78° C. After stirring at -78° C. for approximately 30 minutes, one equivalent of triisopropyl borate is added and the reaction is slowly warmed to room temperature, followed by acidification with aqueous hydrochloric acid to give a 3-benzyloxybenzene boronic acid compound of formula V. ##STR7##

Workup

temperaturethe reaction is slowly warmed to room temperature

Sources & evidence

ORD record: ord-471dccf2c1fa46e28376187520642c3c
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843940

Reaction notes

Loading…