Tetrafluoroboric acid → 2,4-Difluoro-3-methylbenzene diazonium tetrafluoroborate

HRID 2396938Notes

Reaction equation

HRID 2396938 reaction equation
[F:1][C:2]1[C:8]([CH3:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[F:11][B-:12]([F:15])([F:14])[F:13].[H+].[N:17]([O-])=O.[Na+]>O>[F:11][B-:12]([F:15])([F:14])[F:13].[F:1][C:2]1[C:8]([CH3:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[N+:4]#[N:17]

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 127954872,4-Difluoro-3-methylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 233590052,4-Difluoro-3-methylbenzene diazonium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To 2,4-difluoro-3-methylaniline (20 g) are added 42% tetrafluoroboric acid (56 ml) and water (28 ml) under ice cooling and thereto a solution of sodium nitrite (10 g) in water (20 ml) is added dropwise at below 10° C. After dropwise addition, the mixture is stirred at 0° C. for 15 minutes and the formed crystals are filtered, which is washed with a mixture of ethanol--diethyl ether (1:2), then with diethyl ether, followed by drying under reduced pressure to give 2,4-difluoro-3-methylbenzene diazonium tetrafluoroborate (28.95 g), m.p. 114°-115° C.

Workup

  1. additionAfter dropwise addition
  2. filtrationthe formed crystals are filtered
  3. washwhich is washed with a mixture of ethanol--diethyl ether (1:2)
  4. customby drying under reduced pressure

Sources & evidence

ORD record
ord-0cda1ee8d5bd4b29b4b19bad38215574
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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