Hydrochloric Acid → 2-Benzyloxy-5-trifluoromethylphenylboronic acid

HRID 269552

Reaktionsgleichung

Reaktionsgleichung von HRID 269552
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.C(OCC)C.[B:30](OC)([O:33]C)[O:31]C.Cl>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[B:30]([OH:33])[OH:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8470Trimethyl borateHCID 21112927HCID 21112927, VerbindungHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 230053392-Benzyloxy-5-trifluoromethylphenylboronic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-75 °C

Versuchsvorschrift

A solution of 4-benzyloxy-3-iodobenzotrifluoride (15.07 g, 39.85 mmol) in tetrahydrofuran (200 ml) was cooled to −40° C. with stirring under nitrogen. 2M isopropylmagnesium chloride in diethyl ether (39.85 ml, 79.7 mmol) was added dropwise and the mixture stirred at −40° C. for 40 minutes, then cooled to −75° C. Trimethyl borate (8.3 g, 9.2 ml, 79.7 mmol) was added at −75° C. over 10 minutes and the reaction stirred and allowed to reach 0° C. over 1 h. 1M hydrochloric acid (200 ml) was added and the mixture stirred vigorously for 1 h.

Aufarbeitung

  1. stirringthe mixture stirred at −40° C. for 40 minutes
  2. stirringthe reaction stirred
  3. stirringthe mixture stirred vigorously for 1 h.

Quellen und Nachweise

ORD-Eintrag
ord-d4cc6564f742490e98e35efcb57af4de
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446222B2

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