Dimethylformamide → 1-Bromo-2-chloro-4-ethoxybenzene

HRID 1764897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1764897
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].[H-].[Na+].CN(C=O)C.I[CH2:18][CH3:19]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][CH3:19])=[CH:4][C:3]=1[Cl:9]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 70181824-Bromo-3-chlorophenol

Produkt 1

HCID 227356231-Bromo-2-chloro-4-ethoxybenzeneAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The 4-Bromo-3-chloro-phenol (24 mmol, 5 g) in anhydrous THF (50 mL) was added to a stirred solution of NaH (60%) in mineral oil, 120 mmol, 4.8 g) in THF (100 mL) and DMF (42 mL) under N2 at room temperature. This solution stirred for 30 minutes. The iodethane (240 mmol, 19.2 mL) was then added. The solution was stirred and was refluxed overnight. The reaction was cooled and quenched with 1 N HCl (150 mL), extracted into CH2Cl2 (2×150 mL), dried over MgSO4, concentrated in vacuo, and distilled under vacuum yielding 1-bromo-2-chloro-4-ethoxybenzene as a brown oil (4.59 g, 81%). 1H NMR (CDCl3, 300 MHz): δ7.42 (1H, d, J 8.7 Hz), 6.96 (1H, d, J 2.9 Hz), 6.64 (1H, dd, J 8.8 and 2.5 Hz), 3.95 (2H, q, J 7.0 Hz), 1.39 (3H, t, J 7.0 Hz.)

Aufarbeitung

  1. customat room temperature
  2. stirringThe solution was stirred
  3. temperaturewas refluxed overnight
  4. temperatureThe reaction was cooled
  5. customquenched with 1 N HCl (150 mL)
  6. extractionextracted into CH2Cl2 (2×150 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. distillationdistilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1dcc9bad6cd64b4b8ca18fa0e55013fd
Quelldatensatz
uspto-grants-2007_06
Patentnummer
USRE039679E1

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