(3-hydroxyphenyl)boronic Acid → 3-(1,9-Difluoro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenol

HRID 2218699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2218699
[OH:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[CH:12]=[C:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[C:18]=2[CH2:17][CH2:16][C:15]2[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:14]1=2>>[F:24][C:23]1[C:18]2[CH2:17][CH2:16][C:15]3[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:14]=3[C:13](=[CH:12][C:4]3[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=3)[C:19]=2[CH:20]=[CH:21][CH:22]=1

Komponenten

3

Edukt 2

HCID 2734359(3-hydroxyphenyl)boronic AcidHCID 689374405-bromomethylene-1,9-difluoro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Produkt 1

HCID 597702273-(1,9-Difluoro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenolAusbeute 113,1 %

Versuchsvorschrift

Following procedures essentially as described in Example 219, below, and using 3-hydroxyphenyl boronic acid (380 mg, 2.75 mmol) and 5-bromomethylene-1,9-difluoro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (803 mg, 2.75 mmol), provides to 1.04 g of the title compound as crude product. The crude product is purified using column chromatography eluting with 15% EtOAc/hexane to 30% EtOAc/hexane to give 500 mg (60%) product as a light yellow foam, mp 129.5° C. MS (ES) 333 (M−1). HPLC (ISO90-10M) shows 98% at t=2.90 min.

Quellen und Nachweise

ORD-Eintrag
ord-8a6cb08a5f0d465caa62370242caebe5
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07411072B2

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