Bromocyclopentane → Methyl 3-cyclopentyloxy-4-nitrobenzoate

HRID 1383507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383507
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 21187961Methyl 3-cyclopentyloxy-4-nitrobenzoateAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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 1N 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.

Aufarbeitung

  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 1N sodium hydroxide solution (1×200 mL)
  8. customwater (2×200 mL) and then evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-adbb744a0e7d4826ad81926182c29077
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255326B1

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