Potassium Carbonate → 4-Amino-2-fluorobenzonitrile

HRID 386562Notes

Reaction equation

HRID 386562 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].O.O.[Sn](Cl)Cl.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[NH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 61436Stannous chloride dihydrateHCID 27590482-Fluoro-4-nitrobenzonitrile

Product 1

HCID 27834134-Amino-2-fluorobenzonitrileYield 100.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

The mixture of 2-fluoro-4-nitrobenzonitrile (8.31 g, 50 mmol) and tin (II) chloride dihydrate (56.4 g, 250 mmol) in 250 mL of EtOAc was stirred at 25° C. overnight. LCMS (78109-084) indicated the reaction was completed. 25 mL of sat. K2CO3 was added to the reaction. The resulting mixture was stirred at room temperature for 2 h and was followed by addition of 100 g of solid K2CO3. The mixture was stirred at room temperature for 2 hours. Solid was removed by filtration and further washed with EtOAc (50 mL×2). The filtrate was concentrated to yield 6.81 g (100%) of 4-amino-2-fluorobenzonitrile as an off white solid. 1H NMR (400 MHz, CDCl3) δ ppm 4.30 (s, 2H) 6.29-6.51 (m, 2H) 7.27-7.40 (m, 1H). MS (ESI) 137 (M+H).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 h
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. customSolid was removed by filtration
  4. washfurther washed with EtOAc (50 mL×2)
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1032ddf7ac874b9791e16b7b8ff82a5d
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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