3-Ethoxybenzeneboronic acid → 2-tert-Butyl-4-(3-ethoxyphenyl)-5-aminophenol

HRID 74005Notes

Reaction equation

HRID 74005 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].[CH2:16]([O:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)[CH3:17]>CC#N>[C:1]([C:5]1[CH:10]=[C:9]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([O:18][CH2:16][CH3:17])[CH:24]=2)[C:8]([NH2:12])=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27739203-Ethoxybenzeneboronic acidHCID 574702362-Tert-butyl-4-bromo-5-nitrophenol

Product 1

HCID 574702432-tert-Butyl-4-(3-ethoxyphenyl)-5-aminophenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-tert-Butyl-4-(3-ethoxyphenyl)-5-aminophenol (C-16) was synthesized following the general scheme above starting from 2-tert-butyl-4-bromo-5-nitrophenol (C-14-a) and 3-ethoxyphenyl boronic acid. HPLC ret. time 2.77 min, 10-99% CH3CN, 5 min run; ESI-MS 286.1 m/z (MH+).

Sources & evidence

ORD record
ord-73910f44ef1f446f9ad354ba6ba5527f
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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