Water → 2-(4-Bromo-2,6-difluorophenyl)acetic acid

HRID 576196Notes

Reaction equation

HRID 576196 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH2:9][C:10]#N)=[C:4]([F:12])[CH:3]=1.[OH:13]S(O)(=O)=O.[OH2:18]>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH2:9][C:10]([OH:13])=[O:18])=[C:4]([F:12])[CH:3]=1

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 27733112-(4-bromo-2,6-difluorophenyl)acetonitrile

Product 1

HCID 27733092-(4-Bromo-2,6-difluorophenyl)acetic acidYield 33.3%

Procedure

A solution of 2-(4-bromo-2,6-difluorophenyl)acetonitrile (0.5 g, 2.155 mmol) in H2SO4 (3 mL, 56.3 mmol) and H2O (3 mL, 167 mmol) was stirred at 60° C. for 16 h. After LCMS analysis showed the starting material had disappeared, the mixture was dissolved in H2O (20 mL) and extracted by EA (2×30 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by silica column chromatography (PE/EA=3/1 to 1/1) to yield 2-(4-bromo-2,6-difluorophenyl)acetic acid (0.3 g, 0.718 mmol, 33.3% yield): 1H NMR (400 MHz, CD3OD) δ 7.13-7.05 (m, 2H), 3.71 (s, 2H).

Workup

  1. extractionextracted by EA (2×30 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by silica column chromatography (PE/EA=3/1 to 1/1)

Sources & evidence

ORD record
ord-a214c25e8cc342b3abf9f0582a6b9133
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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