Triisopropyl borate → 4-Diethylamino-3-methylphenylboronic acid

HRID 1516646Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[C:4]([CH3:13])[CH:3]=1.C([Li])CCC.[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C>>[CH2:9]([N:8]([CH2:11][CH3:12])[C:5]1[CH:6]=[CH:7][C:2]([B:19]([OH:24])[OH:20])=[CH:3][C:4]=1[CH3:13])[CH3:10]

Participants

Reactant 3

HCID 21531Triisopropyl borate

HCID 666720654-Bromo-N,N-diethyl-2-methylbenzenamine

HCID 178418339Butyllithium

Product 1

HCID 666720564-Diethylamino-3-methylphenylboronic acidYield 111.2%

Procedure

In a manner similar to that of Example 1c, by reacting 8 g of (4-bromo-2-methylphenyl)diethylamine (33 mmol) with 16 mL of a 2.5 M solution of n-butyllithium and 11.5 mL (50 mmol) of triisopropyl borate, 7.6 g of 4-diethylamino-3-methylphenylboronic acid (yield=100%) are obtained in the form of a thick oil.

Sources & evidence

ORD record: ord-d52d09d30ce74cd4b595f643c7471a6a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227507B2

Reaction notes

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