Benzenamine, 4-bromo-N,N-diethyl- → 4-(Diethylamino)phenylboronic acid

HRID 1158156Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:4][CH:3]=1.C([Li])CCC.[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C>>[CH2:9]([N:8]([CH2:11][CH3:12])[C:5]1[CH:6]=[CH:7][C:2]([B:18]([OH:23])[OH:19])=[CH:3][CH:4]=1)[CH3:10]

Participants

Reactant 3

HCID 16328Benzenamine, 4-bromo-N,N-diethyl-

HCID 21531Triisopropyl borate

HCID 178418339Butyllithium

Product 1

HCID 219888814-(Diethylamino)phenylboronic acidYield 94.6%

Procedure

In a manner similar to that of Example 1c, by reacting 5 g of (4-bromo-phenyl)diethylamine (21.9 mmol) with 13 mL of 2.0 M n-butyllithium solution and 6 mL (26 mmol) of triisopropyl borate. 4 g of 4-diethylaminophenylboronic acid (yield=94%) are obtained in the form of a white solid.

Sources & evidence

ORD record: ord-fc93be8a07bf4fa8ba4cc36dfa7850e5
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807708B2

Reaction notes

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