Thiophenol → (4'-Fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-YL)methyl phenyl sulfide

HRID 325534Notes

Reaction equation

HRID 325534 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([CH3:27])[CH:21]=1>CN(C=O)C>[C:1]1([S:7][CH2:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([CH3:27])[CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydride2×HCID 133169812-(4-Fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl chloride

Product 1

HCID 13316982(4'-Fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-YL)methyl phenyl sulfideYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Thiophenol (1.4 ml, 13.6 mmoles) was added dropwise to a stirred suspension of sodium hydride (0.653 g, 13.6 mmoles) in dry DMF under an atmosphere of nitrogen. The mixture was then heated at 50° C. for 30 minutes until all of the sodium hydride was consumed and hydrogen evolution ceased. To this solution was added a solution of 2-chloromethyl-4'-fluoro-3,3',5-trimethyl-1,1'-biphenyl (3.27 g crude, approximately 11.3 mmoles) in 8 ml of dry DMF and the mixture was heated at 50° with stirring for 30 minutes. The reaction was cooled to room temperature and partitioned between ether (200 ml) and dilute sodium hydroxide solution (50 ml). The ether solution was extracted with dilute sodium hydroxide solution (50 ml) again, then extracted with dilute sodium chloride solution (2×100 ml). The ether solution was then dried (MgSO4), filtered, and the solvent was evaporated to leave 3.75 g of product. This material was purified by flash chromatography on silica gel with a 60×150 mm column eluting with methylene chloride/hexane, 1/4 (v:v) to give 3.1 g of the title compound, m.p. 72°-74° C.

Workup

  1. customwas consumed
  2. temperaturethe mixture was heated at 50°
  3. custompartitioned between ether (200 ml) and dilute sodium hydroxide solution (50 ml)
  4. extractionThe ether solution was extracted with dilute sodium hydroxide solution (50 ml) again
  5. extractionextracted with dilute sodium chloride solution (2×100 ml)
  6. dry with materialThe ether solution was then dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-70d45184363d4e72abe6806556f42901
Source dataset
uspto-grants-1984_04
Patent number
US04440927

Reaction notes

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