1-Chloro-4-nitrobenzene → HCID 10659067, compound

HRID 2259680Notes

Reaction equation

HRID 2259680 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S-:9])[CH:6]=[CH:7][CH:8]=1.[K+].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CN(C)C=O>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([S:9][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][CH:6]=2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 74741-Chloro-4-nitrobenzeneHCID 23693163HCID 23693163, compound

Product 1

HCID 10659067HCID 10659067, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of potassium 3-methoxybenzenethiolate (6.37 g, 35.7 mmol) and 4-chloronitrobenzene (5.11 g, 32.5 mmol) in dimethylformamide (30 mL) was stirred at room temperature for 4 hours. The reaction mixture was poured into ice water and a yellow solid was collected by filtration. Recrystallization from 90% ethanol yielded the title anisole (7.79 g, 92%) as a yellow solid; mp 81°-83° C. 1H-NMR (250 MHz, d6-DMSO): 3.80 (s, 3H, OCH3) 7.10-7.19 (m, 3H, aromatic) 7.32 (d, 2H, J=7.1 Hz, aromatic) 7.43-7.49 (m, 1H, aromatic) 8.15 (d, 2H, J=7.0, aromatic). MS (CI, CH4): 262 (M+1). Analysis for C13H11NO3S: Calculated: C, 59.76; H, 4.24; N, 5.36. Found: C, 59.74; H, 4.40; N, 5.34.

Workup

  1. filtrationa yellow solid was collected by filtration
  2. customRecrystallization from 90% ethanol

Sources & evidence

ORD record
ord-2e190377966f431e8fa374068796884f
Source dataset
uspto-grants-1995_12
Patent number
US05474999

Reaction notes

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