Hydrochloric Acid → HCID 18415111, Verbindung

HRID 991978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 991978
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:22])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH:19]([CH3:21])[CH3:20])[CH:13]=1)[C:5](O)=[O:6].B([O-])[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C(Br)C.Cl>C(Cl)Cl.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:22])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH:19]([CH3:20])[CH3:21])[CH:13]=1)[CH2:5][OH:6]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 9932398HCID 9932398, VerbindungHCID 178449041HCID 178449041, Verbindung

Produkt 1

HCID 18415111HCID 18415111, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)benzoic acid (Example 1(c) (1.0 g, 3.3 mmol), tetrabutylammonium boronate (2.6 g, 9.9 mmol) and ethylbromide (1.0 ml, 13.2 mmol) in 25 ml of CH2Cl2 and 10 ml of tetrahydrofuran was stirred at room temperature over night. The reaction mixture was treated with 1M HCl and extracted several times with EtOAc. The combined organic phases were washed once with water followed by a saturated solution of NaCl. After drying over MgSO4, filtration and evaporation, the residue was purified by column chromathography (silica gel, 7:3 p-ether/EtOAc). This gave 0.922 g (98%) of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy) benzyl-alcohol.

Aufarbeitung

  1. extractionextracted several times with EtOAc
  2. washThe combined organic phases were washed once with water
  3. dry with materialAfter drying over MgSO4, filtration and evaporation
  4. customthe residue was purified by column chromathography (silica gel, 7:3 p-ether/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-fdab3f2131fd47e7bec390ade8516305
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465687B1

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