HCID 54323262, compound → HCID 23283986, compound

HRID 370346Notes

Reaction equation

HRID 370346 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[CH:9][C:8]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])=[CH:7][C:6]=1[N+:17]([O-:19])=[O:18]>CN(C)C=O.O>[N+:17]([C:6]1[CH:7]=[C:8]([S:11]([F:16])([F:12])([F:13])([F:14])[F:15])[CH:9]=[CH:10][C:5]=1[C:2]#[N:3])([O-:19])=[O:18]

Participants

5

Reactant 2

HCID 54323262HCID 54323262, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 23283986HCID 23283986, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Copper (I) cyanide (5.05 g) was added to a stirred solution of 4-bromo-3-nitro- phenylsulphur pentafluoride (18.5 g) in N,N- dimethylformamide and heated at 140° C. for 4 hours. A mixture of ferric chloride (20.0 g),concentrated hydrochloric acid and water was added at 105° C. and heating continued for 1.25 hours. The cooled mixture was diluted with water, extracted (ether) and the organic phase washed (water), dried (magnesium sulphate) and evaporated to give 2-nitro-4-pentafluorosulphanylbenzonitrile (14.7 g), m.p.57-59° C.

Workup

  1. additionwas added at 105° C.
  2. temperatureheating
  3. extractionextracted (ether)
  4. washthe organic phase washed (water)
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated

Sources & evidence

ORD record
ord-3757c5987e3840339425c4161d7b2c95
Source dataset
uspto-grants-2000_10
Patent number
US06140528

Reaction notes

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