Water → 4-Bromo-2-chloro-6-methylbenzoic acid

HRID 2427488Notes

Reaction equation

HRID 2427488 reaction equation
[OH2:1].N(OS(=O)(=O)O)=O.[Br:9][C:10]1[CH:18]=C(C)[C:13]([C:14](N)=[O:15])=[C:12]([CH3:20])[CH:11]=1.Cl[CH2:22][Cl:23]>>[Br:9][C:10]1[CH:11]=[C:12]([CH3:20])[C:13]([C:14]([OH:1])=[O:15])=[C:22]([Cl:23])[CH:18]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 82157Nitrosylsulfuric acidHCID 544913594-Bromo-2,6-dimethylbenzamide

Product 1

HCID 566042464-Bromo-2-chloro-6-methylbenzoic acidYield 88%

Procedure

Water (5 mL) was chilled in an ice bath and nitrososulfuric acid was added dropwise. A suspension of 4-Bromo-2,6-dimethyl-benzamide (1.30 g, 5.23 mmol) in dichloromethane (10 mL) was added. The organic phase was dried over magnesium sulfate and concentrated. It was taken up in ethyl acetate and extracted three times with saturated sodium bicarbonate. The combined aqueous extracts were acidified with 6M hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated to provide the title compound as a colourless solid (1.14 g, 88%). 1H NMR CDCl3: δ 7.48 (s, 1H), 7.35 (s, 1H), 2.45 (s, 3H).

Workup

  1. additionwas added
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. extractionextracted three times with saturated sodium bicarbonate
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8f631b3611d042ac8502c89d54753320
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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