Water → HCID 22312899, compound

HRID 351563Notes

Reaction equation

HRID 351563 reaction equation
O.[Br:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[C:5]([Br:12])[C:4]=1[CH:13]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[C:14]#[N:15]>C1COCC1>[NH2:9][C:7]1[CH:6]=[C:5]([Br:12])[C:4]([CH:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:14]#[N:15])=[C:3]([Br:2])[CH:8]=1

Participants

4

Reactant 2

HCID 962Water2×HCID 22312896HCID 22312896, compound

Product 1

HCID 22312899HCID 22312899, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15% TiCl3 in water (0.13 mol) was added dropwise at RT to a solution of (±)-2,6-dibromo-α-(4-chlorophenyl)-4-nitrobenzeneacetonitrile (0.026 mol) in THF (200 ml). The mixture was stirred at RT for 2 hours, poured out into H2O and extracted with CH2Cl2. The organic layer was separated, washed with H2O and with K2CO3 10%, dried, filtered and the solvent was evaporated. A part of this residue (2 g) was crystallized from diethyl ether. The precipitate was filtered off and dried, yielding 1.3 g (±)-4-amino-2,6-dibromo-α-(4-chlorophenyl)benzeneacetonitrile (interm. 47).

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic layer was separated
  3. washwashed with H2O and with K2CO3 10%
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customA part of this residue (2 g) was crystallized from diethyl ether
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-d3632e0d5275457db5957ca629bd524b
Source dataset
uspto-grants-2004_06
Patent number
US06743792B2

Reaction notes

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