Pentane → 2,6-Dimethylphenylboronic acid

HRID 2085591Notes

Reaction equation

HRID 2085591 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].C([Li])(C)(C)C.CCCCC.[B:20](OC)([O:23]C)[O:21]C>O1CCCC1>[CH3:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[B:20]([OH:23])[OH:21]

Participants

6

Reactant 4

HCID 8003PentaneHCID 8470Trimethyl borateHCID 684712-Bromo-m-xyleneHCID 178418306HCID 178418306, compound

Product 1

HCID 5833222,6-Dimethylphenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure A and using 1-bromo-2,6-dimethyl-benzene (Aldrich, 5 g, 27 mmol), 50 mL of anhydrous tetrahydrofuran, 1.7M solution of t-butyllithium in n-pentane (32 mL, 54 mmol) and trimethyl borate (6.05 mL, 54 mmol), the title compound was obtained after recrystallization from ethyl acetate-hexane mixture (0.7 g, 10%).

Sources & evidence

ORD record
ord-75d3164b7c9243f2a6240d27459e121c
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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