Sulfuric Acid → 3-Bromo-2-fluoro-6-methyl-5-nitrobenzoic acid

HRID 1616455Notes

Reaction equation

HRID 1616455 reaction equation
[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:11])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.OS(O)(=O)=O.[Br:20]N1C(C)(C)C(=O)N(Br)C1=O>O>[Br:20][C:3]1[C:2]([F:1])=[C:7]([C:6]([CH3:11])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1)[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 593345776-Fluoro-2-methyl-3-nitrobenzoic acid

Product 1

HCID 866726603-Bromo-2-fluoro-6-methyl-5-nitrobenzoic acidYield 158%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6-fluoro-2-methyl-3-nitrobenzoic acid (100 mg, 0.5 mmol) in concentrated H2SO4 (0.5 ml, 9.38 mmol) was added 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (79 mg, 0.28 mmol) at room temperature and under nitrogen. The reaction mixture was stirred for 6 hours during which time a precipitate formed. The reaction mixture was added slowly to deionized water (3 ml) and the resulting precipitate was filtered. The solid was washed with deionized water (2 ml) and air dried for 2 hours to give 123 mg (88%) of 3-bromo-2-fluoro-6-methyl-5-nitrobenzoic acid as a pale yellow solid. LC-MS 94%, 1.61 min (3 minute LC-MS method), m/z=275.9/277.9 (ES−), 1H NMR (500 MHz, Chloroform-d) δ ppm 8.25 (d, J=6.2 Hz, 1H), 2.58 (s, 3H).

Workup

  1. customformed
  2. filtrationthe resulting precipitate was filtered
  3. washThe solid was washed with deionized water (2 ml) and air
  4. customdried for 2 hours

Sources & evidence

ORD record
ord-ac6671899e1d454bb78d84e44ba42401
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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