Bromocyclopentane → Methyl 3-cyclopentyloxy-4-nitrobenzoate

HRID 356924Notes

Reaction equation

HRID 356924 reaction equation
[CH:1]1(Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[OH:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:17]([O:19][CH3:20])=[O:18]>CN(C)C=O>[CH:1]1([O:13][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[N+:24]([O-:26])=[O:25])[C:17]([O:19][CH3:20])=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 21187961Methyl 3-cyclopentyloxy-4-nitrobenzoateYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopentyl bromide (38.7 g, 0.26 mol) is added slowly (over 1 hour) to a stirred suspension of potassium carbonate (41.4 g, 0.3 mol) in N,N-dimethylformamide (200 mL) containing methyl 3-hydroxy-4-nitrobenzoate (39.4 g, 0.2 mol) at 65° C. and then the stirring is continued for 4 hours. The mixture is allowed to cool and then filtered. The filtrate is diluted with water (700 mL) containing sodium chloride (50 g) and then extracted with toluene (3×200 mL). The combined organic extract is washed with 1 N sodium hydroxide solution (1×200 mL) and then water (2×200 mL) and then evaporated under reduced pressure to give methyl 3-cyclopentyloxy-4-nitrobenzoate (54.2 g, 100%) as a pale green solid which is used without further purification.

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. additionThe filtrate is diluted with water (700 mL)
  4. additioncontaining sodium chloride (50 g)
  5. extractionextracted with toluene (3×200 mL)
  6. extractionThe combined organic extract
  7. washis washed with 1 N sodium hydroxide solution (1×200 mL)
  8. customwater (2×200 mL) and then evaporated under reduced pressure

Sources & evidence

ORD record
ord-445b41f90eec4e948b3fe16dfc8ac900
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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