N,N-Diethylaniline → 3-Bromo-2-(prop-2-en-1-yl)phenol

HRID 1672581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672581
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)C=C.N([C:17]1[CH:22]=CC=C[CH:18]=1)(CC)CC>CCOC(C)=O>[CH2:22]([C:6]1[C:7]([Br:11])=[CH:8][CH:9]=[CH:10][C:5]=1[OH:4])[CH:17]=[CH2:18].[CH2:22]([C:10]1[CH:9]=[CH:8][C:7]([Br:11])=[CH:6][C:5]=1[OH:4])[CH:17]=[CH2:18]

Komponenten

5

Edukt 2

HCID 7061N,N-DiethylanilineHCID 257945Allyl m-bromophenyl ether

Produkt 2

HCID 153607573-Bromo-2-(prop-2-en-1-yl)phenolAusbeute 47 %HCID 15360758HCID 15360758, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
220 °C

Versuchsvorschrift

A mixture of 1-(allyloxy)-3-bromobenzene (3.53 g, 16.6 mmol) and Et2NPh (7.4 mL) was heated in a 220° C. oil bath. After 5 hr, the reaction mixture was cooled to room temperature, diluted with EtOAc (80 mL), and washed with 2N aq HCl (3×20 mL), water (2×20 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (0%-1 0% EtOAc/hexanes) gave 1.64 g (47%) of the title compound as the late eluting component, and 1.19 g (34%) of 2-allyl-5-bromophenol. 1HNMR (300 MHz, CDCl3) δ 7.17 (dd, J=8.0, 1.1, 1H), 6.97 (t, J=8.0, 1H), 6.77 (dd, J=8.0, 1.0, 1H), 6.04-5.90 (m, 1H), 5.15 (t, J=1.7, 1H), 5.13-5.07 (m, 2H), 3.63 (dt, J=6.0, 1.6, 2H).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washwashed with 2N aq HCl (3×20 mL), water (2×20 mL), brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fad8268c960f4bef8bc5b5d38f6bde96
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998993B2

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