Dichloromethane → HCID 59654728, Verbindung

HRID 659106

Reaktionsgleichung

Reaktionsgleichung von HRID 659106
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]1([C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Br:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34](O)=[O:35])[CH:30]=[CH:31][CH:32]=1.C(Cl)Cl>ClC1C=CC=CC=1Cl>[Br:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34]([C:23]2[O:22][C:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:25][CH:24]=2)=[O:35])[CH:30]=[CH:31][CH:32]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 14812Phosphorus oxide (P4O10)HCID 74653(3-Bromophenyl)acetic acidHCID 5193632-Phenylfuran

Produkt 1

HCID 59654728HCID 59654728, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 72391,2-DichlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Phosphorous pentoxide (2.02 g, 14.20 mmol) suspended in 1,2-dichlorobenzene (60 mL) was added to a mixture of 2-phenyl-furan (23) (500 mg, 2.84 mmol) and 3-bromophenylacetic acid (24) (1.34 g, 6.25 mmol). The reaction mixture was heated to 80° C. for 2 hours and then cooled to ambient temperature. DCM was added, the organic layer washed with water and partially reduced in vacuo. The crude product was purified by Flash Master Jones Chromatography using a 50 g silica cartridge and first eluting with heptane to remove excess 1,2-dichlorobenzene, then 5-10% EtOAc in heptane to give the title compound. Yield: 278 mg, 38%; LC-MS tr 1.73 min; HPLC Purity: 100%; MS (ES+) m/z 341, 343 (M+H)

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. washthe organic layer washed with water
  3. customThe crude product was purified by Flash Master Jones Chromatography
  4. washfirst eluting with heptane
  5. customto remove excess 1,2-dichlorobenzene

Quellen und Nachweise

ORD-Eintrag
ord-16232f9a991840aa9087cb202a425d26
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080567B2

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