1-Bromo-2-ethylbenzene → Methyl 3-(4-((2-ethylphenyl)ethynyl)phenyl)propanoate

HRID 2043000

Reaktionsgleichung

Reaktionsgleichung von HRID 2043000
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[CH:2].Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH3:23]>>[CH2:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)[CH3:23]

Komponenten

3

Edukt 2

HCID 160891-Bromo-2-ethylbenzeneHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Produkt 1

HCID 45112274Methyl 3-(4-((2-ethylphenyl)ethynyl)phenyl)propanoate

Versuchsvorschrift

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (95 mg, 0.51 mmol) and 1-bromo-2-ethylbenzene (0.10 mL, 0.73 mmol) according to the general procedure IF to give 130 mg (87%) of a clear oil after purification by flash chromatography (SiO2, EtOAc:PE, 1:7): Rf=0.28 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 7.50-7.48 (m, 1H), 7.46-7.44 (m, 2H), 7.26-7.22 (m, 2H), 7.20-7.14 (m, 3H), 3.67 (s, 3H), 2.96 (t, J=7.8 Hz, 2H), 2.88 (q, J=7.2 Hz, 2H), 2.63 (t, J=7.6 Hz, 2H), 1.29 (t, J=7.6 Hz, 3H); 13C NMR (CDCl3) δ 173.2, 146.3, 140.9, 132.2, 131.8, 128.6, 128.5, 128.1, 125.8, 122.5, 121.7, 92.9, 88.0, 51.8, 35.6, 31.0, 27.9, 14.9; ESI-MS m/z 315.1 (M+Na+).

Quellen und Nachweise

ORD-Eintrag
ord-0375c00ea5e445e1b63e3dc4012694f3
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586607B2

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