Lithium hydroxide, monohydrate → 2-Bromo-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoic acid

HRID 1352039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352039
O.[OH-].[Li+].[Br:4][C:5]1[CH:14]=[C:13]([C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)=[O:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8]>O.O1CCCC1.CO>[Br:4][C:5]1[CH:14]=[C:13]([C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)=[O:16])[CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 235607712-Bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoic acid methyl ester

Produkt 1

HCID 226613232-Bromo-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoic acidAusbeute 102,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of lithium hydroxide monohydrate (4.41 g, 105.1 mmol) in water (15 mL) was added to a solution of 2-bromo-4-[[[(3-hydroxyphenyl)methyl]amino]-carbonyl]benzoic acid, methyl ester (Example 14; 15.30 g, 42.0 mmol) in tetrahydrofuran/methanol (2:1, 21 mL). The solution was stirred at room temperature for 1 h, then it was concentrated to remove tetrahydrofuran and methanol. The remaining aqueous solution was extracted with ethyl acetate (15 mL) and the ethyl acetate extract was discarded. The aqueous layer was acidified with 1 M HCl (75 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (15 mL), dried (MgSO4), filtered, and evaporated to give 2-bromo-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoic acid (15.1 g, quantitative yield) which was used in the next step without further purification.

Aufarbeitung

  1. concentrationit was concentrated
  2. customto remove tetrahydrofuran and methanol
  3. extractionThe remaining aqueous solution was extracted with ethyl acetate (15 mL)
  4. extractionthe ethyl acetate extract
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. washThe combined organic layers were washed with brine (15 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-15aaf82e16a34c46a6c1af4a1be0dc93
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217728B2

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