Sodium Carbonate → 2'-Chloro-4'-(ethylthio)-5-(trifluoromethyl)-[1,1'-biphenyl]-2-ol

HRID 1694711Notes

Reaction equation

HRID 1694711 reaction equation
C1(C)C=CC(P(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.[OH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[Cl:43][C:44]1[CH:49]=[C:48]([S:50][CH2:51][CH3:52])[CH:47]=[CH:46][C:45]=1I>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:43][C:44]1[CH:49]=[C:48]([S:50][CH2:51][CH3:52])[CH:47]=[CH:46][C:45]=1[C:25]1[C:24]([OH:23])=[CH:29][CH:28]=[C:27]([C:30]([F:33])([F:32])[F:31])[CH:26]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 13956Phosphine, tris(4-methylphenyl)-HCID 59436609(2-Hydroxy-5-(trifluoromethyl)phenyl)boronic acidHCID 672801852-Chloro-4-(ethylthio)-1-iodo-benzene

Product 1

HCID 672810892'-Chloro-4'-(ethylthio)-5-(trifluoromethyl)-[1,1'-biphenyl]-2-ol

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of palladium acetate (0.045 g) and tri-p-tolylphosphine (0.213 g) in methanol (10 ml) was stirred at RT for 30 min. The product from step (iii) (1 g), sodium carbonate (1.27 g), the product from example (26) step (i) (1.19 g) and methanol (20 ml) were added and the mixture heated under reflux for 6 h. The solvent was removed under reduced pressure and the residue partitioned between diethylether and 2M hydrochloric acid. The organics were separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 10% ethylacetate/isohexane. Yield 0.503 g

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 6 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue partitioned between diethylether and 2M hydrochloric acid
  5. customThe organics were separated
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica eluting with 10% ethylacetate/isohexane

Sources & evidence

ORD record
ord-c914bdbf71e24bb585e2f0d95f4ed87d
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

Loading…