Ammonium Hydroxide → 4-Amino-2-chloro-6-fluorobenzonitrile

HRID 872609Notes

Reaction equation

HRID 872609 reaction equation
Br[C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:10].[Cu][C:12]#[N:13].[OH-].[NH4+]>CN(C=O)C>[NH2:6][C:5]1[CH:7]=[C:8]([F:9])[C:2]([C:12]#[N:13])=[C:3]([Cl:10])[CH:4]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 671683704-Bromo-3-chloro-5-fluoroanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 596358834-Amino-2-chloro-6-fluorobenzonitrileYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 4-bromo-3-chloro-5-fluoroaniline (2.08 g, 9.27 mmol) and copper(I)cyanide (0.83 g, 9.27 mmol) in DMF (15 ml) was heated in microwave reactor at 190° C. for 1 h. Reaction mixture was poured into 12% ammonium hydroxide (200 ml) and stirred for 30 min. Thus formed precipitate was filtered, washed with water and dried in vacuum to obtain 1.21 g (77%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 6.44 (dd, 1H), 6.60 (m, 1H), 6.86 (bs, 2H).

Workup

  1. customReaction mixture
  2. filtrationThus formed precipitate was filtered
  3. washwashed with water
  4. customdried in vacuum

Sources & evidence

ORD record
ord-5b48e14112ac42a2a895bc645c690c69
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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