2-Chloro-5-nitroanisole → HCID 10825354, compound

HRID 865060Notes

Reaction equation

HRID 865060 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([S-:7])=[CH:3][CH:2]=1.[K+].Cl[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[O:19][CH3:20]>CN(C)C=O>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([S:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[C:11]([O:19][CH3:20])[CH:12]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 705192-Chloro-5-nitroanisoleHCID 23708194HCID 23708194, compound

Product 1

HCID 10825354HCID 10825354, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of potassium 4-pyridinethiolate (20.00 g, 134 mmol) and 2-chloro-5-nitroanisole (20.91 g, 112 mmol) in dimethylformamide (80 mL) was stirred at room temperature for 24 hours. The reaction mixture was poured into ice water and a brown solid was collected by filtration. The solid was stirred with 3N HCl (400 mL) for 30 minutes, and the solution filtered. The filtrate was basified with ammonium hydroxide with cooling in an ice bath. Filtration of the basic solution yielded the title anisole as an orange solid (26.23 g, 90%); mp 133°-135° C. 1H-NMR (300 MHz, d6-DMSO): 3.95 (s, 3H, OCH3) 7.24 (dd, 2H, J=4.6, 1.7 Hz, aromatic) 7.53 (d, 1H, J=8.3 Hz, aromatic) 7.88 (dd, 2H, J=8.3, 2.3 Hz, aromatics) 8.48 (dd, 2H, J=4.7, 1.3 Hz, aromatic). MS (CI, CH4): 263 (M+1).

Workup

  1. filtrationa brown solid was collected by filtration
  2. filtrationthe solution filtered
  3. temperaturewith cooling in an ice bath
  4. filtrationFiltration of the basic solution

Sources & evidence

ORD record
ord-5765122b2d754e6692808caa747a3d85
Source dataset
uspto-grants-1996_10
Patent number
US05565465

Reaction notes

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