Sulfuric Acid → Flurbiprofen Methyl Ester

HRID 1870839Notes

Reaction equation

HRID 1870839 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S(=O)(=O)(O)O.[C:24](=O)(O)[O-].[Na+]>CO.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9]([O:11][CH3:24])=[O:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 3394FlurbiprofenHCID 516892Sodium Bicarbonate

Product 1

HCID 4127Flurbiprofen Methyl Ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

2-(2-Fluoro-biphenyl-4-yl)-propionic acid (104.2 g) was dissolved in methanol (410 ml) and then conc. sulfuric acid (60.2 g) was added, after which the resulting mixture was stirred at 40° C. for 2.5 hours. The mixture was cooled to room temperature, diluted with toluene, then neutralized with a saturated aqueous sodium bicarbonate solution, and thereafter subjected to extraction with ethyl acetate. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure, to obtain methyl 2-(2-fluoro-biphenyl-4-yl)-propionate (110.2 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionsubjected to extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-249cc11b715b41a28cd30b8eefbbdcd3
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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