Hydrochloric Acid → HCID 22312920, compound

HRID 965635Notes

Reaction equation

HRID 965635 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[Cl:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:18]([Cl:25])[C:17]=1Cl.Cl>C1COCC1.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.[OH-].[Na+]>[Cl:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:18]([Cl:25])[C:17]=1[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:11]([F:12])([F:13])[F:14])[CH:4]=1)[C:9]#[N:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 883653,4,5-TrichloronitrobenzeneHCID 50046852-(4-Chloro-3-(trifluoromethyl)phenyl)acetonitrile

Product 1

HCID 22312920HCID 22312920, compoundYield 86.5%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-chloro-3-(trifluoromethyl)benzeneacetonitrile (0.114 mol) in THF (100 ml) was added dropwise at RT to a solution of 1,2,3-trichloro-5-nitrobenzene (0.114 mol) and N,N,N-triethylbenzenemethanaminium chloride (3 g) in NaOH 150 ml) and THF (100 ml). The mixture was stirred at RT for 2 hours, then poured out on ice, acidified with a concentrated HCl solution and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 40.4 g (86.5%) of (±)-2,6-dichloro-α-[4-chloro-3-(trifluoromethyl)phenyl]-4-nitrobenzeneacetonitrile (interm. 1).

Workup

  1. additionpoured out on ice
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was crystallized from DIPE
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-4ca63dff65be4a4eb8be900a9e1113d7
Source dataset
uspto-grants-2005_10
Patent number
US06951857B2

Reaction notes

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