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

HRID 1459092Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].B(OC)(OC)OC.F[C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[B:21]([OH:23])[OH:22].[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>>[F:20][C:19]1[CH:14]=[C:15]([B:21]([OH:23])[OH:22])[CH:16]=[CH:17][C:18]=1[O:27][CH2:26][CH2:25][CH2:24][CH2:28][CH2:1][CH2:2][CH2:3][CH3:4]

Participants

Reactant 4

HCID 8028Tetrahydrofuran2×

HCID 8470Trimethyl borate

HCID 2734333(2,3-Difluorophenyl)boronic acid

HCID 178418339Butyllithium

Product 1

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

Procedure

Quantities: compound 11 (10.00 g, 0.033 mol) in anhydrous THF (132 ml), n-butyllithium (16 ml, 2.5M in hexane, 0.04 mol), trimethyl borate (6.87 g, 0.066 mol) in anhydrous THF (50 ml). The experimental procedure was as described for the preparation of compound 2.

Sources & evidence

ORD record: ord-8c54cafe745b4408b9532a39c9137552
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05853613

Reaction notes

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