2,5-Dichlorophenol → 4-(2,5-Dichlorophenoxy)-3-nitrobenzonitrile

HRID 1184379Notes

Reaction equation

HRID 1184379 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].Cl[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 662,5-DichlorophenolHCID 11430Potassium CarbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-

Product 1

HCID 595489424-(2,5-Dichlorophenoxy)-3-nitrobenzonitrileYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,5-Dichlorophenol (17.86 g, 109.54 mmol) and 4-chloro-3-nitrobenzonitrile (10.00 g, 54.77 mmol) were combined with K2CO3 (37.85 g, 273.85 mmol) in THF (300 mL). The reaction mixture was refluxed for 48 hrs and then the solid was filtered over a bed of Celite. After rinsing the residue with copious amounts of DCM, the filtrate was concentrated to produce a yellow solid. The solid was triturated with minimal DCM and collected via vacuum filtration to yield compound 34 (13.84 g, 81.7% yield, 100.0% pure). 1H NMR (500 MHz, DMSO-d6): δ 8.73 (s, 1H), 8.12 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.73 (d, J=9 Hz, 1H), 7.65 (d, J=2 Hz, 1H), 7.48 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.21 (d, J=9 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 48 hrs
  2. filtrationthe solid was filtered over a bed of Celite
  3. washAfter rinsing the residue with copious amounts of DCM
  4. concentrationthe filtrate was concentrated
  5. customto produce a yellow solid
  6. customThe solid was triturated with minimal DCM
  7. filtrationcollected via vacuum filtration

Sources & evidence

ORD record
ord-ad89e1cfcb494aba98d01bbe7d370ca8
Source dataset
uspto-grants-2014_03
Patent number
US08669247B2

Reaction notes

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