6-Isopropyl-o-toluidine → HCID 14534569, compound

HRID 1886555Notes

Reaction equation

HRID 1886555 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([CH3:11])[CH3:10])[C:3]=1N.B(F)(F)[F:13].F.N([O-])=O.[Na+]>O>[F:13][C:3]1[C:5]([CH:9]([CH3:11])[CH3:10])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 789206-Isopropyl-o-toluidineHCID 9855450Trifluoroborane HydrofluorideHCID 23668193Sodium Nitrite

Product 1

HCID 14534569HCID 14534569, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

44.7 g (0.3 mole) of 2-methyl-6-isopropylaniline are added dropwise to 200 ml of 40% strength tetrafluoboric acid at 5° C., followed by a solution of 20.7 g of sodium nitrite in 20 ml of water. The mixture is stirred for 1 hour at 10° C. The precipitated diazonium tetrafluoborate is filtered off under suction and suspended in succession in 50 ml of ice water, 50 ml of cold ethanol and 50 ml of diethyl ether. The suspension is added dropwise to a flask preheated at 150° C. When the evolution of gas has ended, the product is obtained by distillation over a Claisen still (bath temperature 100° C., pressure 4 mbar, distillation temperature 41°-42° C.). 28 g (61%) of 2-fluoro-3-isopropyltoluene are obtained.

Workup

  1. filtrationThe precipitated diazonium tetrafluoborate is filtered off under suction
  2. additionThe suspension is added dropwise to a flask
  3. custompreheated at 150° C
  4. customthe product is obtained by distillation over a Claisen still (bath temperature 100° C., pressure 4 mbar, distillation temperature 41°-42° C.)

Sources & evidence

ORD record
ord-aed0236560c141f2889c65dc1ad7bf5f
Source dataset
uspto-grants-1992_09
Patent number
US05151548

Reaction notes

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