HCID 131734215, compound → HCID 84776658, compound

HRID 1497543Notes

Reaction equation

HRID 1497543 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[C:4]([F:10])[C:3]=1[CH2:11][CH2:12][C:13]([O:15]C(C)(C)C)=[O:14]>Br>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([F:10])[C:3]=1[CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

3

Reactant 1

HCID 131734215HCID 131734215, compound

Product 1

HCID 84776658HCID 84776658, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

tert-Butyl 3 (2,6-difluoro-4-methoxyphenyl)propanoate (11.7 g) was suspended in 48% aqueous hydrogen bromide (200 mL), followed by stirring at 120 □ C for 16 hours. The reaction mixture was concentrated under reduced pressure, and then to the residue was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 3-(2,6-difluoro-4-hydroxyphenyl)propanoic acid (3.17 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added water
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5b71a232e49943eaba6b4f11bbb0bd97
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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