Benzene → 4-Ethynyl-2-fluoro-1-methylbenzene

HRID 564670Notes

Reaction equation

HRID 564670 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9]C(C)(O)C)[CH:5]=[CH:4][C:3]=1[CH3:14].[OH-].[Na+].C1C=CC=CC=1>O>[F:1][C:2]1[CH:7]=[C:6]([C:8]#[CH:9])[CH:5]=[CH:4][C:3]=1[CH3:14]

Participants

5

Reactant 3

HCID 241BenzeneHCID 14798Sodium HydroxideHCID 22112194HCID 22112194, compound

Product 1

HCID 221123164-Ethynyl-2-fluoro-1-methylbenzeneYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 2-fluoro-4-(3-methyl-3-hydroxy-1-butynyl)toluene (0.035 mol), sodium hydroxide (0.07 mol), and benzene 40 ml was refluxed for 3 hours. After cooling, water 40 ml was added and the mixture was thoroughly stirred. Insoluble materials were filtered away with Celite (trade name of Johns-Manville Company), and the residue was dried over anhydrous magnesium sulfate. The drying agent was separated away, the solvent was carefully distilled away from the solution under reduced pressure, the residue was purified by silica gel chromatography (elution liquid: hexane) and then distilled away the solvent under reduced pressure (boiling point: 100° C., 20 mmHg) to obtain cororless oily 2-fluoro-4-ethynyltoluene (0.014 mol).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. filtrationInsoluble materials were filtered away with Celite (trade name of Johns-Manville Company)
  4. dry with materialthe residue was dried over anhydrous magnesium sulfate
  5. customThe drying agent was separated away
  6. distillationthe solvent was carefully distilled away from the solution under reduced pressure
  7. customthe residue was purified by silica gel chromatography (elution liquid: hexane)
  8. distillationdistilled away the solvent under reduced pressure (boiling point: 100° C., 20 mmHg)

Sources & evidence

ORD record
ord-e35aea6ebd5e486b825592a0cde6eb47
Source dataset
uspto-grants-2001_01
Patent number
US06168728A

Reaction notes

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