Hydrochloric Acid → 2-Bromo-4-methoxybenzoic acid

HRID 1363420Notes

Reaction equation

HRID 1363420 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([N+]([O-])=O)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][O-:15].[Na+].Cl>CS(C)=O>[Br:1][C:2]1[CH:10]=[C:9]([O:15][CH3:14])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3135342-Bromo-4-nitrobenzoic acidHCID 10942334Sodium Methoxide

Product 1

HCID 144847132-Bromo-4-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Bromo-4-nitrobenzoic acid (3 g, 12.2 mmol) was reacted with sodium methoxide (6 g, 111 mmol) in dry DMSO (250 mL) at 80° C. After completion of reaction mixture was poured over crushed ice, acidified with 1:1 HCl and extracted with EtOAc (3×150 mL). The organic layer was concentrated to obtain the title compound.

Workup

  1. customAfter completion of reaction mixture
  2. additionwas poured
  3. customover crushed ice
  4. extractionextracted with EtOAc (3×150 mL)
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-ccd2b7bdf5cc4372b3aaf2630c887c5f
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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