Sulfuric Acid → 4'-Ethyl-2-fluoro-1,1'-biphenyl

HRID 2399140Notes

Reaction equation

HRID 2399140 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[CH:5][CH:4]=1)#[CH:2].S(=O)(=O)(O)O.[H][H]>[Pd].C1C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 42040FluretofeneHCID 178418361HCID 178418361, compound4×

Product 1

HCID 224077014'-Ethyl-2-fluoro-1,1'-biphenyl

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

1-Ethynyl-4-(2-fluorophenyl)benzene, 22 g, was reduced in a Parr Instrument Company Series 3910 Low Pressure Shaker-type Apparatus, using 100 ml of benzene, 2 g of five percent palladium on charcoal, and 0.5 ml of concentrated sulfuric acid. Reduction was carried out at room temperature and at an initial hydrogen pressure of 50 psig. Within 15 minutes, the hydrogen pressure had dropped to 32 psig. Hydrogen pressure was increased to 52 psig and agitation continued for two hours, with no additional hydrogen pressure drop. The reaction mixture was filtered and the filtrate was neutralized with two percent aqueous sodium carbonate. The resulting mixture was washed with water. The benzene phase was separated, dried over anhydrous sodium sulfate, and filtered. The benzene was evaporated and the residue was vacuum distilled to give 17 g of 1-ethyl-4- (2-fluorophenyl)benzene, bp 99°-101°/0.3 mm. The following elemental analysis was obtained:

Workup

  1. filtrationThe reaction mixture was filtered
  2. washThe resulting mixture was washed with water
  3. customThe benzene phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe benzene was evaporated
  7. distillationdistilled

Sources & evidence

ORD record
ord-3b471213d8034485a11c81656014aa33
Source dataset
uspto-grants-1977_05
Patent number
US04027041

Reaction notes

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