Hydrochloric Acid → 3-Bromo-5-(hydroxymethyl)benzoic acid

HRID 14101

Reaktionsgleichung

Reaktionsgleichung von HRID 14101
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13]C)=[O:12])[CH:10]=1)[C:5](O)=[O:6].[BH4-].[Li+].C(O)C.Cl>O1CCCC1>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([CH2:5][OH:6])[CH:3]=1)[C:11]([OH:13])=[O:12]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4148881Lithium borohydrideHCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

Produkt 1

HCID 81671273-Bromo-5-(hydroxymethyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice-cold solution of 3-bromo-5-(methoxycarbonyl)benzoic acid prepared by the method in Preparation 2 (10.3 g, 40 mmol) in anhydrous tetrahydrofuran (100 mL) is added lithium borohydride (12 g, 550 mmol) portion-wise. The reaction is stirred 4 h at this temperature. Absolute ethanol (20 mL) is added dropwise, and the reaction is stirred 1.5 h. The reaction is slowly poured on ice, and 10% hydrochloric acid (aq) is added until gas evolution ceased. The aqueous layer is extracted with chloroform, and the organic layer is washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 229, 231 [M−H]−.

Aufarbeitung

  1. stirringthe reaction is stirred 1.5 h
  2. additionis added until gas evolution
  3. extractionThe aqueous layer is extracted with chloroform
  4. washthe organic layer is washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-479f562303ec43e8b64ace9bb92a85a5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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