Sodium Hydroxide → 2-[4-(2-Bromoethoxy)naphthalen-1-yl]-1-benzofuran-3-carboxylic acid

HRID 1287932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1287932
Br[O-].[Na+].BrBr.[OH-].[Na+].[C:8]([C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]=1[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([O:30][CH2:31][CH2:32][Br:33])=[CH:22][CH:21]=1)(=[O:10])C.S(=O)(O)[O-:35].[Na+]>O.O1CCOCC1>[C:8]([C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]=1[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([O:30][CH2:31][CH2:32][Br:33])=[CH:22][CH:21]=1)([OH:10])=[O:35]

Komponenten

8

Edukt 5

HCID 14798Sodium HydroxideHCID 24408BromineHCID 215070481-{2-[4-(2-Bromoethoxy)naphthalen-1-yl]-1-benzofuran-3-yl}ethan-1-oneHCID 23665763Sodium BisulfiteHCID 23673712Sodium hypobromite

Produkt 1

HCID 215070562-[4-(2-Bromoethoxy)naphthalen-1-yl]-1-benzofuran-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of sodium hypobromite, prepared by adding 2.45 g. (0.45 mol.) of bromine to a cooled (0°) solution of 4.5 g. (0.1125 mol.) of sodium hydoxide in 40 ml. of water, was added to a solution of 6.1 g. (0.015 mol.) of 3-acetyl-2-[4-(2-bromoethoxy)naphthyl]benzofuran in 60 ml. of dioxane and the mixture was shaken for 12 hours. Sodium bisulfite was added to the reaction mixture, water was added and the mixture was extracted twice with ether. The aqueous phase was acidified with hydrochloric acid, the resulting precipitate was digested on a steam bath for 1 hour, cooled to 0° and collected by filtration to give 3-carboxy-2-[4-(2-bromo-ethoxy)naphthyl]benzofuran, m.p. 260°-265° (dec.).

Aufarbeitung

  1. additionby adding 2.45 g
  2. additionwas added
  3. extractionthe mixture was extracted twice with ether
  4. temperaturecooled to 0°
  5. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-517b80626db2429f8b30a3a513baeedd
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03985896

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