Nitrosylsulfuric acid → 4-Bromo-2-methoxy-6-methylbenzoic acid

HRID 2427489Notes

Reaction equation

HRID 2427489 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6](N)=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.N(OS(=O)(=O)O)=[O:15]>C(Cl)Cl.O>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:15])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

5

Reactant 2

HCID 82157Nitrosylsulfuric acidHCID 57949645HCID 57949645, compound

Product 1

HCID 454803864-Bromo-2-methoxy-6-methylbenzoic acidYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Bromo-2-methoxy-6-methylbenzamide (2.0 g, 8.2 mmol), dissolved in CH2Cl2, was added dropwise to nitrosyl sulfuric acid (14.0 mL) in water (6.0 mL) at 0° C. and stirred for 2 hours. The reaction mixture was poured over ice and extracted with CH2Cl2, and the solvent was removed under reduced pressure to afford a light pink solid (1.93 g, 96%). 1H NMR (300 MHz, CDCl3): δ 7.07 (s, 1H), 7.00 (s, 1H), 3.93 (s, 3H), 2.46 (s, 3H).

Workup

  1. additionThe reaction mixture was poured over ice
  2. extractionextracted with CH2Cl2
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-275a25ad57844f80b74d5fa2acd944ae
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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