Tetrahydrofuran → HCID 11108683, compound

HRID 440157Notes

Reaction equation

HRID 440157 reaction equation
O1CCCC1.[Cl:6][C:7]1[CH:13]=[C:12]([Cl:14])[C:11]([F:15])=[CH:10][C:8]=1[NH2:9].[F:16][B-:17]([F:20])([F:19])[F:18].[H+].[N:22]([O-])=O.[Na+]>O>[F:16][B-:17]([F:20])([F:19])[F:18].[Cl:6][C:7]1[CH:13]=[C:12]([Cl:14])[C:11]([F:15])=[CH:10][C:8]=1[N+:9]#[N:22]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 28118Tetrafluoroboric acidHCID 27580982,4-Dichloro-5-fluoroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 11108683HCID 11108683, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

165 ml of tetrahydrofuran are added to 100 g of 2,4-dichloro-5-fluoroaniline at room temperature. To this solution are added 333 ml of tetrafluoroboric acid (50% strength) with cooling. 57.5 g of sodium nitrite in 117 ml of water are added to the reaction mixture cooled to 5°-10° C. in such a way that the internal temperature is 7°-13° C. After addition is completed, the 0° C. solution is filtered. The residue is washed with tetrahydrofuran and ice-cold water. 121 g of product remain.

Workup

  1. temperaturewith cooling
  2. temperaturecooled to 5°-10° C. in such a way that the internal temperature
  3. customis 7°-13° C
  4. additionAfter addition
  5. filtrationthe 0° C. solution is filtered
  6. washThe residue is washed with tetrahydrofuran and ice-cold water

Sources & evidence

ORD record
ord-75ccc428b7784551b3c69c9012b774d2
Source dataset
uspto-grants-1996_05
Patent number
US05516932

Reaction notes

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