1,1'-Biphenyl, 4-(bromomethyl)- → 1-(2-Biphenyl-4-yl-1-phenyl-ethyl)-1H-benzotriazole

HRID 724633

Reaktionsgleichung

[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:26][CH:25]=1>O1CCCC1>[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][C:24]([CH2:23][CH:1]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[N:9]2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:29][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A solution of 1-benzyl-1H-1,2,3-benzotriazole (750 mg, 3.6 mmol) in tetrahydrofuran (36 mL) was cooled to −78° C. and treated with n-butyllithium (2.8 mL, 1.6 M in hexanes) dropwise. The reaction mixture was stirred at −78° C. for 10 min and 4-bromomethyl-biphenyl (1.0 g, 4.1 mmol) in tetrahydrofuran (4 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h, quenched with sat. ammonium chloride (100 mL), and extracted with ethyl acetate (150 mL). The organic layer was separated and washed with brine (50 mL), dried with sodium sulfate, filtered, and concentrated to a white solid. This material was triturated with diethyl ether (2×50 mL) to yield the desired product (1.12 g, 83%). LCMS found for C26H22N3 (M+H)+: m/z=376.

Aufarbeitung

stirringThe reaction mixture was stirred at −78° C. for 1 h
customquenched with sat. ammonium chloride (100 mL)
extractionextracted with ethyl acetate (150 mL)
customThe organic layer was separated
washwashed with brine (50 mL)
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated to a white solid
customThis material was triturated with diethyl ether (2×50 mL)

Quellen und Nachweise

ORD-Eintrag: ord-1d742bfcfbad42edb21b57e3f9c1a024
Quelldatensatz: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07141596B2

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