Ammonia → 4-Amino-2-chloro-6-fluorobenzonitrile

HRID 1409308Notes

Reaction equation

HRID 1409308 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].CN1C(=O)CCC1.N>O>[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

6

Reactant 4

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 671683704-Bromo-3-chloro-5-fluoroanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 596358834-Amino-2-chloro-6-fluorobenzonitrileYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

4-Bromo-3-Chloro-5-fluoroaniline (980 mmol, 220 g), copper(I)cyanide (980 mmol, 88 g) and NMP (1000 ml) were added into the reaction flask, heated up to 160° C. and stirred for 3 h to complete the reaction. The reaction mixture was cooled to RT. Water and 25% ammonia solution was added keeping the mixture at RT. The mixture was stirred overnight and the formed precipitate was separated by filtration and flushed with water. The filtered precipitate was dried under vacuum to give 117.7 g of the title compound. 1H-NMR (400 MHz, DMSO-d6): δ 6.41-6.47 (m, 1H), 6.58-6.62 (m, 1H), 6.86 (bs, 2H).

Workup

  1. customthe reaction
  2. temperatureThe reaction mixture was cooled to RT
  3. customat RT
  4. stirringThe mixture was stirred overnight
  5. customthe formed precipitate was separated by filtration
  6. customflushed with water
  7. customThe filtered precipitate was dried under vacuum

Sources & evidence

ORD record
ord-47b86430debb4c03a6dd09ac183176b2
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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