Potassium Carbonate → HCID 66666161, compound

HRID 474238Notes

Reaction equation

HRID 474238 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 692642-Chloro-5-nitrophenolHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 66666161HCID 66666161, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-5-nitrophenol (10 g, 57.6 mmol) in acetonitrile (100 mL) was added potassium carbonate (11.7 g, 86 mmol) followed by 4-methoxy benzyl bromide (13.9 g, 69.1 mmol), at room temperature. The reaction mixture was stirred at room temperature for 18 h while monitoring by TLC. It was then filtered and the solid mass was washed with ethyl acetate (100 mL). The solvent was removed under reduced pressure and the residue was purified by column chromatography (60-120 mesh silica gel) using 2% MeOH in CHCl3 to give 1-chloro-2-(4-methoxybenzyloxy)-4-nitrobenzene (15 g, 89%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.85 (1H, s), 7.79 (1H, d, J=8.8 Hz), 7.53-7.51 (1H, d, J=8.4 Hz), 7.41-7.39 (2H, m), 6.95-6.87 (2H, m), 5.17 (2H, s), 3.82 (3H, s).

Workup

  1. filtrationIt was then filtered
  2. washthe solid mass was washed with ethyl acetate (100 mL)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography (60-120 mesh silica gel)

Sources & evidence

ORD record
ord-38eb90833ffe45f1bf6c16e4dd8ba6fe
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

Loading…