Hydrochloric Acid → 2-Bromo-4-methoxybenzoic acid

HRID 2355775Notes

Reaction equation

HRID 2355775 reaction equation
BrBr.[OH-].[Na+].[Br:5][C:6]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:7]=1[C:8](C1C=CC=CC=1)=[O:9].S([O-])([O-])=[O:23].[Na+].[Na+].Br[O-].[Na+].Cl>>[Br:5][C:6]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:7]=1[C:8]([OH:9])=[O:23]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 24437Sodium SulfiteHCID 123194602-Bromo-4-methoxy benzophenoneHCID 23673712Sodium hypobromite

Product 1

HCID 144847132-Bromo-4-methoxybenzoic acidYield 95%

Procedure

In an ice bath, bromine (2.8 mL, 35.1 mmol) is slowly added dropwise into an aqueous NaOH (4.5 g, 111.4 mmol) solution (10 mL) and stirred for 10 mins. Then 2-bromo-4-methoxy benzophenone (2.1 g, 9.2 mmol) is added dropwise into the reaction, and stirred for 15 hrs at the temperature. After completion of the reaction, aqueous sodium sulfite is added to eliminate the unreacted sodium hypobromite. The resultant mixture is extracted with ethyl acetate to isolate neutral compound. The aqueous phase is then acidified with 6N HCl in an ice bath to give large quantities of white solid. The resultant is filtered under vacuum to give white solid (IV) (2.0 g, 95%).

Workup

  1. stirringstirred for 15 hrs at the temperature
  2. additionis added
  3. extractionThe resultant mixture is extracted with ethyl acetate
  4. customto isolate neutral compound
  5. customto give large quantities of white solid
  6. filtrationThe resultant is filtered under vacuum

Sources & evidence

ORD record
ord-9e2ac048c65041efb0897bb97494d180
Source dataset
uspto-grants-2010_07
Patent number
US07754891B2

Reaction notes

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