3,5-Difluorotoluene → 2-(2,6-Difluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 521914Notes

Reaction equation

HRID 521914 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18](O)C)[CH:5]=[C:6]([F:17])[C:7]=1[B:8]1[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]1.FC1C=C(C)C=C(F)C=1.C([Li])CCC>>[F:17][C:6]1[CH:5]=[C:4]([CH3:18])[CH:3]=[C:2]([F:1])[C:7]=1[B:8]1[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]1

Participants

4

Reactant 3

HCID 27783293,5-DifluorotolueneHCID 867138511-(3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanolHCID 178418339Butyllithium

Product 1

HCID 666564462-(2,6-Difluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Procedure

Following the procedure of Intermediate 106, replacing 1-(3,5-difluorophenyl)ethanol with 1,3-difluoro-5-methylbenzene, and reducing the number of equivalents of butyl lithium to 1.05 provided the title compound.

Sources & evidence

ORD record
ord-8658fd2bf4564d1199b070be6365ecae
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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