Bromocyclopentane → HCID 21187914, compound

HRID 356923

Reaction equation

HRID 356923 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:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])[C:17]([OH:19])=[O:18]>CN1CCN(C)C1=O>[CH:1]1([O:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=2[N+:23]([O-:25])=[O:24])[C:17]([O:19][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 692653-Hydroxy-4-nitrobenzoic acid

Product 1

HCID 21187914HCID 21187914, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

Cyclopentyl bromide (20g, 134 mmol) is added slowly (over 30 minutes) to a stirred suspension of potassium carbonate (27.6 g, 200 mmol) in N,N'-dimethylimidazolidinone (75 mL) containing 3-hydroxy-4-nitrobenzoic acid (9.15 g, 50 mmol) at 85° C. and then stirring is continued for 14 hours. The mixture is allowed to cool and then filtered. The filtrate is diluted with water (100 mL) then extracted with toluene (2×100 mL). The combined organic extract is dried over magnesium sulfate and then the solvent is removed under reduced pressure to give a brown mobile oil. This oil is subjected by flash chromatography on silica gel (dichloromethane as eluent) and the eluent evaporated under reduced pressure to give cyclopentyl 3-cyclopentyloxy-4-nitrobenzoate (10.2 g, 81.6%) as a yellow solid m.p. 45.5-°46.5° C. [Elemental analysis: C,63.7; H,6.66; N,4.37%; calculated: C,63.93; H,6.63; N, 4.39%].

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. additionThe filtrate is diluted with water (100 mL)
  4. extractionthen extracted with toluene (2×100 mL)
  5. extractionThe combined organic extract
  6. dry with materialis dried over magnesium sulfate
  7. customthe solvent is removed under reduced pressure
  8. customto give a brown mobile oil
  9. customthe eluent evaporated under reduced pressure

Sources & evidence

ORD record
ord-3b0e1a0879e544feafbcf8e466559db3
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Linked notes

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