1-Chloro-4-nitrobenzene → 2-(5-chloro-2-nitrophenyl)acetonitrile

HRID 2187631Notes

Reaction equation

HRID 2187631 reaction equation
ClC1C=CC([N+]([O-])=O)=CC=1.ClC1C=CC(OCC#N)=CC=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[Cl:46][C:47]1[CH:48]=[CH:49][C:50]([N+:56]([O-:58])=[O:57])=[C:51]([CH2:53][C:54]#[N:55])[CH:52]=1.[F:59][C:60]1[CH:61]=[C:62]([CH:65]=[CH:66][CH:67]=1)[CH2:63]Br>C(#N)C>[Cl:46][C:47]1[CH:48]=[CH:49][C:50]([N+:56]([O-:58])=[O:57])=[C:51]([CH2:53][C:54]#[N:55])[CH:52]=1.[Cl:46][C:47]1[CH:48]=[CH:49][C:50]([N+:56]([O-:58])=[O:57])=[C:51]([CH:53]([CH2:63][C:62]2[CH:65]=[CH:66][CH:67]=[C:60]([F:59])[CH:61]=2)[C:54]#[N:55])[CH:52]=1

Participants

9

Reactant 6

HCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 680073-Fluorobenzyl bromideHCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 27752682-(5-chloro-2-nitrophenyl)acetonitrile

Product 2

HCID 27752682-(5-chloro-2-nitrophenyl)acetonitrileHCID 18476408HCID 18476408, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(5-Chloro-2-nitrophenyl)acetonitrile was prepared from 4-chloronitrobenzene and 4-chlorophenoxyacetonitrile according to procedure known in the art (M. Makosza, J. Winiarski, J. Org. Chem. 1984, 49, 1494). To a suspension of 13.8 g (0.1 mol) anhydrous potassium carbonate in 100 ml acetonitrile were added 100 mg 18-crown-6, 3.93 g (20.0 mmol) of (5-chloro-2-nitrophenyl)acetonitrile, and 4.15 g (21.95 mmol) 3-fluorobenzyl bromide, successively. It was stirred at room temperature overnight, and the solids were removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was stirred with a small amount of ethanol to give the pale yellow crystalline title compound, which was collected by filtration, washed with cold ethanol, and dried in vacuo.

Workup

  1. customthe solids were removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. stirringthe residue was stirred with a small amount of ethanol

Sources & evidence

ORD record
ord-a1ff3e23b31847e8991510042e9ceee9
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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