Bromocyclopentane → Methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate

HRID 1095762Notes

Reaction equation

HRID 1095762 reaction equation
[OH:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].Br[CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:18]1([O:1][C:2]2[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 59268115Methyl 3-hydroxy-4-methoxy-2-nitrobenzoate

Product 1

HCID 66781723Methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 3-hydroxy-4-methoxy-2-nitrobenzoate (1.14 g, 5.0 mmol), bromocyclopentane (0.7 mL, 6.5 mmol), potassium carbonate (2.0 g, 14 mmol), and anhydrous acetonitrile (15 mL) was refluxed under N2. After 19 h, the reaction was allowed to cool to room temperature, concentrated, and purified by silica gel chromatography (4:1→3:2; hexanes:ethyl acetate) to give methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate: MS (ESI): 296.5.

Workup

  1. temperaturewas refluxed under N2
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography (4:1→3:2; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-d65596030e66412eaecd3601da7b1681
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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