Nitric Acid → 3-Bromo-4-(2'-methylbutyl)benzoic acid

HRID 2072606Notes

Reaction equation

HRID 2072606 reaction equation
[CH3:1][C@@H:2]([CH2:13][CH3:14])[CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[N+]([O-])(O)=O.[Br:19]Br>O.[N+]([O-])([O-])=O.[Ag+]>[Br:19][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[CH2:3][CH:2]([CH3:1])[CH2:13][CH3:14])[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 24408BromineHCID 141773954-((2s)-2-Methylbutyl)benzoic acid

Product 1

HCID 198599663-Bromo-4-(2'-methylbutyl)benzoic acidYield 39.1%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

A solution of silver nitrate (177 g, 1.1 mol) in water (500 ml) was dropwise added to a solution in water (500 ml), of a mixture of (S)-4-(2'-methylbutyl)benzoic acid (200 g, 1.0 mol), nitric acid (680 ml) and bromine (183 g, 1.1 mol), under ice-cooling, followed by agitating the mixture at room temperature for 5 hours, feeding it into ice water, filtering deposited crystals, adding a 10% sodium carbonate aqueous solution (2 l), sufficiently agitating the mixture, filtering off a remaining insoluble substance, acidifying the filtrate with sulfuric acid, filtering deposited crystals and recrystallizing from acetic acid (1 l) to obtain 3-bromo-4-(2'-methylbutyl)benzoic acid (106.0 g, m.p. 78.8°-79.7° C.).

Workup

  1. temperaturecooling
  2. filtrationfiltering
  3. additionadding a 10% sodium carbonate aqueous solution (2 l)
  4. stirringsufficiently agitating the mixture
  5. filtrationfiltering off a remaining insoluble substance
  6. filtrationfiltering
  7. customrecrystallizing from acetic acid (1 l)

Sources & evidence

ORD record
ord-cd3797faa672467c8c466356f2c389be
Source dataset
uspto-grants-1990_04
Patent number
US04913838

Reaction notes

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