Calcium Carbonate → HCID 86605682, Verbindung

HRID 860964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860964
[Br-:1].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([O-])([O-])=O.[Ca+2].[Cl:42][C:43]1[C:44]([CH3:64])=[C:45]([CH:49]=[C:50]([Cl:63])[C:51]=1[O:52][C:53]1[CH:58]=[CH:57][C:56]([OH:59])=[C:55]([CH:60]([CH3:62])[CH3:61])[CH:54]=1)[C:46]([OH:48])=[O:47]>CO.C(Cl)Cl>[Cl:42][C:43]1[C:44]([CH3:64])=[C:45]([CH:49]=[C:50]([Cl:63])[C:51]=1[O:52][C:53]1[CH:54]=[C:55]([CH:60]([CH3:61])[CH3:62])[C:56]([OH:59])=[C:57]([Br:1])[CH:58]=1)[C:46]([OH:48])=[O:47]

Komponenten

5

Edukt 3

HCID 10112Calcium CarbonateHCID 21339097HCID 21339097, VerbindungHCID 53442637Benzyltrimethylammoniumtribromide

Produkt 1

HCID 86605682HCID 86605682, VerbindungAusbeute 32,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

A suspension of benzyltrimethylamonium tribromide (2.2 g, 5.63 mmol) and CaCO3 (0.28 g, 2.82 mmol) was stirred for 2 hr at 20° C. in a 1:1 MeOH/CH2Cl2 solution (10 mL) containing 3,5-dichloro-2-methyl-4-(4-hydroxy-3-isopropylphenoxy)-benzoic acid (1.0 g, 2.82 mmol). Once HPLC analysis indicated that conversion to the desired monobrominated phenol was optimal, the reaction was quenched by addition of 15 mL of 1N HCl. After removal of the organic solvents under vacuum using a rotary evaporator, the aqueous suspension was extracted twice with EtOAc. After drying the combined EtOAc layers over MgSO4, the salts were filtered prior to removal of the EtOAc under vacuum. The resulting residue after purification by gradient elution from a reverse phase C18 column employing MeOH/H2O containing 0.1% TFA yielded 3,5-dichloro-2-methyl-4-(3-bromo-4-hydroxy-5-isopropylphenoxy)benzoic acid (400 mg).

Aufarbeitung

  1. customthe reaction was quenched by addition of 15 mL of 1N HCl
  2. customAfter removal of the organic solvents under vacuum
  3. customa rotary evaporator
  4. extractionthe aqueous suspension was extracted twice with EtOAc
  5. dry with materialAfter drying the combined EtOAc layers over MgSO4
  6. filtrationthe salts were filtered
  7. customto removal of the EtOAc under vacuum
  8. customThe resulting residue after purification
  9. washby gradient elution from a reverse phase C18 column

Quellen und Nachweise

ORD-Eintrag
ord-f2c5fe9231f34969b5e0a285847f479d
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153997B2

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