Lithium hydroxide, monohydrate → 3-Bromo-5-[(dimethylamino)methyl]benzoic acid

HRID 1617399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617399
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:11]=1)[C:5]([O:7]C)=[O:6].O.[OH-].[Li+]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:11]=1)[C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 58187962Methyl 3-bromo-5-((dimethylamino)methyl)benzoate

Produkt 1

HCID 584313873-Bromo-5-[(dimethylamino)methyl]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 3-bromo-5-[(dimethylamino)methyl]benzoate (0.30 g, 1.1 mmol, from Step A) was dissolved in tetrahydrofuran (20 mL) and lithium hydroxide monohydrate (0.555 g, 13.2 mmol) in water (6 mL) was added. After stirring for 3 hours, the mixture was rotovapped to remove THF and reduce the volume of water. The mixture was diluted with an equivalent volume of acetonitrile and filtered. The product was purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Solvent was removed from fractions containing desired product by rotary evaporation to afford a white solid. Yield: 0.26 g (91%); LC-MS: 258.0, 260.0 (M+H)+. 1H NMR (300 MHz, DMSO-d6): δ 7.86 (dd, 1H), 7.76 (dd, 1H), 7.43 (dd, 1H), 3.38 (s, 2H), 2.14 (s, 6H).

Aufarbeitung

  1. customto remove THF
  2. additionThe mixture was diluted with an equivalent volume of acetonitrile
  3. filtrationfiltered
  4. customThe product was purified via preparative HPLC-MS (C18
  5. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)
  6. customSolvent was removed from fractions
  7. additioncontaining desired product
  8. customby rotary evaporation
  9. customto afford a white solid

Quellen und Nachweise

ORD-Eintrag
ord-c3d6e8d697464cc888a7884b38cb622b
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765734B2

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