3-Nitrophenylboronic Acid → 3-Aminophenylboronic acid

HRID 1786088Notes

Reaction equation

HRID 1786088 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([B:10]([OH:12])[OH:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[Mg]>C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]([B:10]([OH:12])[OH:11])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 5462224Magnesium

Product 1

HCID 922693-Aminophenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-bromonaphthalene 1, magnesium powder in THF is irradiated for 15 min to produce Grignard reagent 2 which reacts with tributyl borate to yield the boronic ester 3. Hydrolysis of 3 with aqueous sulfuric acid affords 1-naphthalene boronic acid 4 (Song, Y; Ding, Z; Wang, Q; Tao, F. Syn. Comm. 1998, 28, 3757, WO 9964428).

Workup

  1. customis irradiated for 15 min

Sources & evidence

ORD record
ord-4b18b52d33e240e49e431631b2bc0b9a
Source dataset
uspto-grants-2009_03
Patent number
US07507262B2

Reaction notes

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