Hydrochloric Acid → HCID 21531926, compound

HRID 1657923Notes

Reaction equation

HRID 1657923 reaction equation
Cl.[CH2:2]([C:6]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:9][C:7]=1N)[CH:3]([CH3:5])[CH3:4].N([O-])=O.[Na+].[F:21][B-](F)(F)F.[NH4+]>O>[F:21][C:7]1[CH:9]=[C:10]([CH2:13][CH:14]([CH3:15])[CH3:16])[CH:11]=[CH:12][C:6]=1[CH2:2][CH:3]([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9964072Ammonium fluoroborateHCID 21531250HCID 21531250, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21531926HCID 21531926, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 124 parts of 6N hydrochloric acid is added 48.8 parts of 2,5-diisobutylaniline. The mixture is cooled to 0° and a cold solution of 17.3 parts of sodium nitrite in water is added slowly, keeping temp. at 0°. A cold solution of 35 parts of ammonium fluoroborate in 120 parts of water is added with vigorous stirring. After one half hour, the precipitate is collected, washed with 25 parts cold 5% ammonium fluoroborate solution, 30 parts cold methanol and ether. The 2,5-diisobutylbenzenediazonium fluoroborate is air dried. The salt is placed in a flask with tube connecting to a second cooled flask and heated until decomposition begins. Sufficient heat to maintain gentle decomposition is continued. When decomposition is complete, the 2-fluoro-1,4-diisobutylbenzene is taken up in ether, washed with dilute sodium hydroxide and water and dried. Removal of the ether gives 2-fluoro-1,4-diisobutylbenzene which can be purified by distillation under reduced pressure.

Workup

  1. temperatureThe mixture is cooled to 0°
  2. customat 0°
  3. waitAfter one half hour
  4. customthe precipitate is collected
  5. washwashed with 25 parts cold 5% ammonium fluoroborate solution, 30 parts cold methanol and ether
  6. customdried
  7. customThe salt is placed in a flask with tube
  8. customconnecting to a second cooled flask
  9. temperatureheated until decomposition
  10. temperatureSufficient heat
  11. temperatureto maintain gentle decomposition
  12. washwashed with dilute sodium hydroxide and water
  13. customdried
  14. customRemoval of the ether

Sources & evidence

ORD record
ord-c3fd291ae2ce4fcca0a256a408fa8c3c
Source dataset
uspto-grants-1976_06
Patent number
US03962307

Reaction notes

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