Ethanol → Ethyl 6-bromonaphthalene-2-carboxylate

HRID 324225

Reaktionsgleichung

Reaktionsgleichung von HRID 324225
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[CH2:15](O)[CH3:16].S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5]2

Komponenten

4

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 45498526-Bromo-2-naphthalenecarboxylic acid2×

Produkt 1

HCID 1249959Ethyl 6-bromonaphthalene-2-carboxylate

Versuchsvorschrift

To a solution of 6-bromo-2-naphthalenecarboxylic acid (Compound M) 3.1 g, (12.43 mmol) in ethanol (30 ml, 23.55 g, 511.0 mmol) was added 18M sulfuric acid (2 ml). The solution was Tefluxed for 30 minutes, cooled to room temperature, and the reaction mixture partitioned between pentane (100 ml) and water (100 ml). The aqueous phase was extracted with pentane (100 ml) and the combined organic layers washed with saturated aqueous NaCl (100 ml), dried MgSO4), and concentrated to yield an off-white solid. Purification by flash chromatography (silica, 10% EtOAc-hexane) afforded the title compound as a white solid. 1H NMR (CDCl3): δ 8.58 (1H, br s), 8.10 (1H, dd, J=1.7, 9 Hz), 8.06 (1H, d, J=2 Hz), 7.83 (1H, d, J=9 Hz), 7.80 (1H, d, J=9 Hz), 7.62 (1H, dd, J=2, 9 Hz).

Aufarbeitung

  1. customfor 30 minutes
  2. customthe reaction mixture partitioned between pentane (100 ml) and water (100 ml)
  3. extractionThe aqueous phase was extracted with pentane (100 ml)
  4. washthe combined organic layers washed with saturated aqueous NaCl (100 ml), dried MgSO4), and
  5. concentrationconcentrated
  6. customto yield an off-white solid
  7. customPurification by flash chromatography (silica, 10% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7f7a5872e19d461387095ee136dc3a75
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218128B1

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