Bromocyclopentane → 1-Cyclopentyloxy-2-methoxy-5-nitrobenzene

HRID 1078611Notes

Reaction equation

HRID 1078611 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].[CH:13]1(Br)[CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH:13]1([O:12][C:4]2[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8728BromocyclopentaneHCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 113907411-Cyclopentyloxy-2-methoxy-5-nitrobenzeneYield 74.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methyloxy-5-nitrophenol (14.27 g, 84.4 mmol) was dissolved in dry dimethylformamide (80 ml). Cyclopentylbromide (176 g, 127 ml, 118.2 mmol) and cesium carbonate (38.5 g, 118.2 mmol) were added and the suspension stirred overnight at room temperature. The mixture was poured into saturated Na2CO3 (200 ml) and extracted with ethyl acetate (700 ml). The organic layer was washed with saturated Na2CO3 until no yellow colour was detected. The organic layer was then dried (MgSO4) and concentrated in vacuo to give the title Compound as a yellow solid (15.0 g).

Workup

  1. extractionextracted with ethyl acetate (700 ml)
  2. washThe organic layer was washed with saturated Na2CO3 until no yellow colour
  3. dry with materialThe organic layer was then dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a4de3e9ae9d4be9a4e3ab95b56a0821
Source dataset
uspto-grants-1996_08
Patent number
US05550137

Reaction notes

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