3-(Methoxycarbonyl)benzeneboronic acid → 2-tert-Butyl-4-(3-methoxycarbonylphenyl)-5-aminophenol

HRID 74006Notes

Reaction equation

HRID 74006 reaction equation
[C:1]([C:5]1[CH:10]=[C:9](Br)[C:8]([N+:12]([O-])=O)=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH3:16][O:17][C:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)=[O:19]>CC#N>[C:1]([C:5]1[CH:10]=[C:9]([C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([C:18]([O:17][CH3:16])=[O:19])[CH:25]=2)[C:8]([NH2:12])=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 574702362-Tert-butyl-4-bromo-5-nitrophenol

Product 1

HCID 574702442-tert-Butyl-4-(3-methoxycarbonylphenyl)-5-aminophenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-tert-Butyl-4-(3-methoxycarbonylphenyl)-5-aminophenol (C-17) was synthesized following the general scheme above starting from 2-tert-butyl-4-bromo-5-nitrophenol (C-14-a) and 3-(methoxycarbonyl)phenylboronic acid. HPLC ret. time 2.70 min, 10-99% CH3CN, 5 min run; ESI-MS 300.5 m/z (MH+).

Sources & evidence

ORD record
ord-ff1b2ee7f6544ed087c57a8b2e5b6e16
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

Loading…