Triisopropyl borate → 4-Diethylamino-3-ethylphenylboronic acid

HRID 1261527Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[C:4]([CH2:13][CH3:14])[CH:3]=1.C([Li])CCC.[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C>>[CH2:9]([N:8]([CH2:11][CH3:12])[C:5]1[CH:6]=[CH:7][C:2]([B:20]([OH:25])[OH:21])=[CH:3][C:4]=1[CH2:13][CH3:14])[CH3:10]

Participants

Reactant 3

HCID 21531Triisopropyl borate

HCID 66672004(4-Bromo-2-ethylphenyl)diethylamine

HCID 178418339Butyllithium

Product 1

HCID 666717804-Diethylamino-3-ethylphenylboronic acidYield 35%

Procedure

In a manner similar to that of Example 1c, by reacting 3 g of (4-bromo-2-ethylphenyl)diethylamine (11.7 mmol) with 5.2 mL of a 2.5 M solution of n-butyllithium and 3.2 mL (14 mmol) of triisopropyl borate, 0.9 g of 4-diethylamino-3-ethylphenylboronic acid (yield=35%) is obtained in the form of a white solid.

Sources & evidence

ORD record: ord-84880f5cc302469b8edff61d791ab96b
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470871B2

Reaction notes

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