Sulfur → Flurbiprofen

HRID 444336Notes

Reaction equation

HRID 444336 reaction equation
[CH3:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:8]([F:18])[CH:7]=1)[C:3]([OH:5])=[O:4].[S]>C1(OC2C=CC=CC=2)C=CC=CC=1.CC(C)=O>[CH3:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([F:18])[CH:7]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 5362487SulfurHCID 23464965HCID 23464965, compound

Product 1

HCID 3394FlurbiprofenYield 45.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of 5.00 g of α-methyl-4-cyclohexyl-3-fluorophenylacetic acid (m.p. 83° to 84° C.) and 2.3 g of sulphur in 10 ml of diphenyl ether was subjected to heating with stirring at 250° C. for 6 hours. The resulting reaction liquid was dissolved in acetone, and the insoluble substances were removed by filtration. The filtrate was poured into an aqueous sodium hydroxide solution. The resulting mixture was repeatedly washed with benzene, and hydrochloric acid was added to the aqueous layer. The crystals thus precipitated were collected by filtration, and recrystallized from a mixed benzene-n-hexane solvent to obtain 2.2 g of α-methyl-2-fluoro-4-biphenylylacetic acid (m.p. 112° to 114° C.).

Workup

  1. temperatureto heating
  2. customThe resulting reaction liquid
  3. customthe insoluble substances were removed by filtration
  4. additionThe filtrate was poured into an aqueous sodium hydroxide solution
  5. washThe resulting mixture was repeatedly washed with benzene, and hydrochloric acid
  6. additionwas added to the aqueous layer
  7. customThe crystals thus precipitated
  8. filtrationwere collected by filtration
  9. customrecrystallized from a mixed benzene-n-hexane solvent

Sources & evidence

ORD record
ord-e87e10e244364eea92a55caa72b9a382
Source dataset
uspto-grants-1981_04
Patent number
US04263457

Reaction notes

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