Hydrochloric Acid → 2-Benzyloxy-5-chlorobenzeneboronic acid

HRID 269544Notes

Reaction equation

C([Li])CCC.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1I)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[B:22](OC(C)C)([O:27]C(C)C)[O:23]C(C)C.Cl>C1COCC1>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[B:22]([OH:27])[OH:23])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Butyllithium (11.5 ml, 28.7 mmol, 2.5 M) was added, under nitrogen, over 10 minutes, to a solution of 2-benzyloxy-5-chloro-iodobenzene (9 g, 26.2 mmol) in THF (40 ml) at −100° C. The reaction mixture was then warmed up at −78° C. and stirred for 1 hour (at −78° C.) before triisopropyl borate (18 ml, 78.4 mmol) was added over 10 minutes. The reaction mixture was then warmed to room temperature before a solution of HCl (60 ml, 1M) was added. The mixture was vigorously stirred for 1½ hours. The organic phase was separated, washed sequentially with water and brine, dried (MgSO4) filtered and concentrated. The residue was triturated with a 30% solution of ether in iso-hexane and filtered to give the title compound (3.62 g, 53%) as a white solid.

Workup

additionwas added over 10 minutes
additionwas added
customThe organic phase was separated
washwashed sequentially with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was triturated with a 30% solution of ether in iso-hexane
filtrationfiltered

Sources & evidence

ORD record: ord-5dba3b35439647478ccef5b491d82e13
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446222B2

Reaction notes

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