Acetic Acid → 3-bromo-4-ethylbenzoic acid

HRID 1434574Notes

Reaction equation

HRID 1434574 reaction equation
[N+]([O-])(O)=O.CC(O)=O.[CH2:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH3:10].[Br:20]Br>O.[N+]([O-])([O-])=O.[Ag+]>[Br:20][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:11]=1[CH2:9][CH3:10])[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 120864-Ethylbenzoic AcidHCID 24408Bromine

Product 1

HCID 73033683-bromo-4-ethylbenzoic acid

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of conc. HNO3 (66 mL), glacial AcOH (300 mL) and water (50 mL), 4-ethyl-benzoic acid (15 g) was added, stirring vigorously, before treating with bromine (5.67 mL). Finally a solution of AgNO3 (16.97 g) in water (50 mL) was added dropwise and the mixture was stirred vigorously for 2 h. The precipitate was collected by filtration, washed well with water, before being extracted with hot, saturated K2CO3 solution, and then treated with charcoal. The hot solution was filtered through kieselguhr and the solution was acidified to pH1 using conc. HCl. The resulting white precipitate was collected by filtration and dried in the vacuum oven overnight at 60° C. to afford the title compound (19.46 g).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred vigorously for 2 h
  3. filtrationThe precipitate was collected by filtration
  4. washwashed well with water
  5. extractionbefore being extracted with hot, saturated K2CO3 solution
  6. additiontreated with charcoal
  7. filtrationThe hot solution was filtered through kieselguhr
  8. filtrationThe resulting white precipitate was collected by filtration
  9. customdried in the vacuum oven overnight at 60° C.

Sources & evidence

ORD record
ord-6b38447425c141cea0784351b0a2dfb2
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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