Sulfuric Acid → 2-(4-Bromo-2,3-difluorophenyl)acetic acid

HRID 1050036Notes

Reaction equation

HRID 1050036 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](CC#N)=[C:4]([F:11])[C:3]=1[F:12].OS(O)(=O)=O.[CH3:18][C:19](=[O:23])[O:20]CC>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:18][C:19]([OH:20])=[O:23])=[C:4]([F:11])[C:3]=1[F:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 904160312-(4-Bromo-2,3-difluorophenyl)acetonitrile

Product 1

HCID 299220662-(4-Bromo-2,3-difluorophenyl)acetic acidYield 41.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

Compound 2-(4-bromo-2,3-difluorophenyl)acetonitrile (200 mg, 0.690 mmol) was dissolved in H2O (1 mL) and H2SO4 (1 mL) at 20° C. in one charge. The reaction mixture was stirred at 100° C. for 1 h. Then the solution was distributed between EA and H2O. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The resulting 2-(4-bromo-2,3-difluorophenyl)acetic acid (180 mg, 0.287 mmol, 41.6% yield) was used in the next step without further purification. TLC (PE/EA=2:1, Rf 0.6): 1H NMR (400 MHz, CDCl3) δ 7.27-7.20 (m, 1H), 6.92-6.85 (m, 1H), 3.65 (s, 2H); ES-LCMS m/z 250.0 (M+H).

Workup

  1. extractionThe combined organic extract
  2. washwas washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e7a57050a4fa49059969775549f6fb99
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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