Benzene, 2-bromo-1,4-dimethyl- → Methyl 3-(4-((2,5-dimethylphenyl)ethynyl)phenyl)propanoate

HRID 2043001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2043001
[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]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[CH3:23]>>[CH3:23][C:17]1[CH:18]=[CH:19][C:20]([CH3:22])=[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

Komponenten

3

Edukt 2

HCID 11121Benzene, 2-bromo-1,4-dimethyl-HCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Produkt 1

HCID 45112275Methyl 3-(4-((2,5-dimethylphenyl)ethynyl)phenyl)propanoate

Versuchsvorschrift

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (95 mg, 0.50 mmol) and 2-bromo-1,4-dimethylbenzene (0.08 mL, 0.60 mmol) according to the general procedure IF to give 123 mg (84%) of a clear oil after purification by flash chromatography (SiO2, EtOAc:PE, 1:8): Rf=0.21 (EtOAc:PE, 1:8); 1H NMR (CDCl3) δ 7.46-7.43 (m, 2H), 7.31 (s, 1H), 7.19-7.17 (m, 2H), 7.11-7.10 (m, 1H), 7.04-7.02 (m, 1H), 3.67 (s, 3H), 2.96 (t, J=7.8 Hz, 2H), 2.63 (t, J=7.8 Hz, 2H), 2.45 (s, 3H), 2.30 (s, 3H); 13C NMR (CDCl3) δ 173.5, 140.8, 137.2, 135.2, 132.4, 131.8, 129.5, 129.3, 128.5, 123.0, 121.7, 93.0, 88.4, 51.8, 35.6, 31.0, 20.9, 20.3; ESI-MS m/z 315.1 (M+Na+).

Quellen und Nachweise

ORD-Eintrag
ord-5b78185ec6b046a2b8a35ec547e1cd94
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586607B2

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