Triisopropyl borate → Boronic acid, [3-fluoro-4-(octyloxy)phenyl]-

HRID 343252Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[C:4]([F:17])[CH:3]=1.C([Li])CCC.C([O:26][B:27](OC(C)C)[O:28]C(C)C)(C)C>>[F:17][C:4]1[CH:3]=[C:2]([B:27]([OH:28])[OH:26])[CH:7]=[CH:6][C:5]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Reactant 3

HCID 21531Triisopropyl borate

HCID 3581959Benzene, 4-bromo-2-fluoro-1-(octyloxy)-

HCID 178418339Butyllithium

Product 1

HCID 10611926Boronic acid, [3-fluoro-4-(octyloxy)phenyl]-

Procedure

This was prepared using a similar method to that described for compound 5. Quantities: 1-bromo-3-fluoro-4-octoxybenzene (15 g, 0.05 mol), n-butyllithium (5 ml, 10M in hexane, 0.05 mol), tri-isopropylborate (18.81 g, 0.1 mol).

Workup

customThis was prepared

Sources & evidence

ORD record: ord-aa9188e7d9fa41eb84aa59de167ab655
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05861109

Reaction notes

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