Nitric Acid → HCID 67273342, compound

HRID 2262863Notes

Reaction equation

HRID 2262863 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[N+:11]([O-])([OH:13])=[O:12]>CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1422285-Bromo-2-methoxyphenol

Product 1

HCID 67273342HCID 67273342, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In SCHEME 7 4-bromoguaiacol (28) is selectively nitrated with 70% HNO3 in AcOH to give 4-bromo-6-nitroguaiacol (29) which is further methylated with methyl iodide and K2CO3 in acetone to give the corresponding 5-bromo-3-nitroveratrol (30). 5-bromo-3-nitroveratrol (30) is reacted under inert conditions with a boronic acid of generell type (31) under Suzuki-type basic conditions (Pd(PPh3)4 and aqueous sodium bicarbonate in dimethoxyethane) to a biaryl of type (32). Biaryl (32) is further hydrolized with aqueous lithium hydroxide in THF and MeOH or MeCN to give the corresponding carboxylic acid (33) which is converted to a building block of type (34) by reaction with oxalyl chloride in anhydrous dichloromethane.

Sources & evidence

ORD record
ord-c725247c0c8542cfa9e7dff624497823
Source dataset
uspto-grants-2010_12
Patent number
US07851501B2

Reaction notes

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