Hydrochloric Acid → 2-(2-Fluorobiphenyl-4-yl)-2-hydroxypropanoic acid

HRID 1659642Notes

Reaction equation

HRID 1659642 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([F:14])[CH:3]=1.[Mg].[C:16]([O-:21])(=[O:20])[C:17]([CH3:19])=[O:18].[Na+].Cl>O1CCCC1>[F:14][C:4]1[CH:3]=[C:2]([C:17]([OH:18])([CH3:19])[C:16]([OH:21])=[O:20])[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5210634-Bromo-2-fluoro-1,1'-biphenylHCID 5462224MagnesiumHCID 23662274Sodium pyruvate

Product 1

HCID 233109062-(2-Fluorobiphenyl-4-yl)-2-hydroxypropanoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-bromo-2-fluorobiphenyl (5 g., 0.02 mole) in dry tetrahydrofuran (20 ml.) was added dropwise, with stirring, to magnesium turnings (0.49 g.) in dry tetrahydrofuran (13 ml.). When the addition was complete, the mixture was stirred and boiled under reflux for one hour. A suspension of sodium pyruvate (2.2 g., 0.02 mole) in dry tetrahydrofuran (20 ml.) was added rapidly to the refluxing solution. Frothing occurred and when this had subsided the mixture was boiled under reflux with stirring for a further hour. The mixture was then cooled in an ice-bath and dilute hydrochloric acid (5 N; 50 ml.) was added. The mixture was stirred and extracted with ether. The extract was then extracted with aqueous potassium carbonate (1 N) and this extract acidified with dilute hydrochloric acid. The precipitate which separated, was collected and dried to give 2-(2-fluoro-4-biphenylyl)-2-hydroxypropionic acid, m.p. 166°-9° C. in 71% yield.

Workup

  1. additionWhen the addition
  2. temperatureunder reflux for one hour
  3. additionwas added rapidly to the refluxing solution
  4. temperatureunder reflux
  5. stirringwith stirring for a further hour
  6. temperatureThe mixture was then cooled in an ice-bath
  7. stirringThe mixture was stirred
  8. extractionextracted with ether
  9. extractionThe extract was then extracted with aqueous potassium carbonate (1 N)
  10. customThe precipitate which separated
  11. customwas collected
  12. customdried

Sources & evidence

ORD record
ord-57d02f3ff84b4b238c07b587b55a971c
Source dataset
uspto-grants-1981_12
Patent number
US04304931

Reaction notes

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