1-Bromopropane → 1-Iodo-4-propoxybenzene

HRID 625889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 625889
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 78401-BromopropaneHCID 10340Sodium CarbonateHCID 108944-Iodophenol

Produkt 1

HCID 132969221-Iodo-4-propoxybenzeneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 4-iodophenol (3 g, 13.64 mmol), 1-bromopropane (1.845 g, 15.00 mmol), and sodium carbonate (7.54 g, 54.5 mmol) in DMF (30 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was diluted with water (250 mL) and extracted with EtOAc (3×75 mL). The combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL), and then dried over MgSO4. The solvent was removed. The crude product (3.11 g) was obtained, which was directly used for the next reaction without further purification. 1H NMR (400 MHz, chloroform-d) δ 7.61-7.53 (m, 2H), 6.74-6.67 (m, 2H), 3.90 (t, J=6.5 Hz, 2H), 1.88-1.76 (m, 2H), 1.05 (t, J=7.4 Hz, 3H).

Aufarbeitung

  1. extractionextracted with EtOAc (3×75 mL)
  2. washThe combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-366ce2d833d5422c8c97f48f5b992598
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09308236B2

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