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

HRID 1618103Notes

Reaction equation

HRID 1618103 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4](N)=[O:5].N([O-])=[O:14].[Na+].[N+]([O-])=O.O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:14])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 23668193Sodium NitriteHCID 67194626HCID 67194626, compoundHCID 178526396Nitrogen Dioxide

Product 1

HCID 450735472-Bromo-4-fluoro-6-methylbenzoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
20 °C

Procedure

2-Bromo-4-fluoro-6-methylbenzamide (0.9 g, 3.9 mmol) was dissolved in 75% aqueous sulfuric acid (4 mL) at 80° C. sodium nitrite (0.5 g, 7.2 mmol) was carefully added in small portions during 1 hour. At the end of addition a persistent color of nitrogen dioxide appeared. The reaction mixture was chilled to 20° C. and cold water (15 mL) was added to the reaction mixture. The product was extracted with ethyl acetate (6×2 mL). The organic phase was washed with water (4×2 mL), brine (2×2 mL), dried with sodium sulfate, filtered and concentrated to give 0.879 g (97%) of pure acid.

Workup

  1. additionwas carefully added in small portions during 1 hour
  2. extractionThe product was extracted with ethyl acetate (6×2 mL)
  3. washThe organic phase was washed with water (4×2 mL), brine (2×2 mL)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9ca63b1280dc436abb967eeb2aa32cfb
Source dataset
uspto-grants-2014_07
Patent number
US08765972B2

Reaction notes

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