Tetrafluoroboric acid → HCID 14534572, compound

HRID 1886560Notes

Reaction equation

HRID 1886560 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:6]=1N)([CH3:4])([CH3:3])[CH3:2].[F:13][B-](F)(F)F.[H+].N([O-])=O.[Na+]>O>[F:13][C:6]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:12]

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 831552-tert-Butyl-6-methylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 14534572HCID 14534572, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

157 g (0.96 mole) of 2-tert-butyl-6-methylaniline are added dropwise to 500 ml of 40% strength tetrafluoroboric acid at 50° C., followed by a solution of 66.2 g (0.96 mole) of sodium nitrite in 270 ml of water. The mixture is stirred for 1 hour at 10° C. The precipitated diazonium salt is filtered off under suction, washed in succession with 50 ml of ice water, 50 ml of cold ethanol and 50 ml of diethyl ether and then suspended in 500 ml of liquid paraffin. The suspension is then added dropwise to a flask preheated at 150° C. After evolution of gas is ended, the product is obtained by distillation over a Claisen still (bath temperature 140° C., pressure 26 mbar) at a distillation temperature of 83° C. 47 g (29%) of 2-fluoro-3-tert-butyltoluene are obtained.

Workup

  1. filtrationThe precipitated diazonium salt is filtered off under suction
  2. washwashed in succession with 50 ml of ice water, 50 ml of cold ethanol and 50 ml of diethyl ether
  3. additionThe suspension is then added dropwise to a flask
  4. custompreheated at 150° C
  5. customthe product is obtained by distillation over a Claisen still (bath temperature 140° C., pressure 26 mbar) at a distillation temperature of 83° C

Sources & evidence

ORD record
ord-be5b3a03cffa4fccb71d26d35559a19c
Source dataset
uspto-grants-1992_09
Patent number
US05151548

Reaction notes

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