Diethyl Ether → 5-Bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran

HRID 22924

Reaktionsgleichung

Reaktionsgleichung von HRID 22924
[CH3:1][C:2]1([CH3:11])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[CH2:3]1.[Br:12]N1C(=O)CCC1=O.CCOCC>ClC(Cl)C>[Br:12][C:9]1[CH:8]=[CH:7][C:5]2[O:6][C:2]([CH3:11])([CH3:1])[CH2:3][C:4]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 806402,3-Dihydro-2,2-dimethylbenzofuran

Produkt 1

HCID 2194755-Bromo-2,2-dimethyl-2,3-dihydro-1-benzofuranAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

2,2-Dimethyl-2,3-dihydrobenzo[b]furan (prepared according to the method of Baker and Shulgin, J. Org. Chem., 28, 1963, 2468) (500 mg, 3.38 mmol) was taken up in dichloroethane (5.5 ml) and stirred at room temperature under nitrogen, and N-bromosuccinimide (661 mg, 3.72 mmol) added in one portion. The reaction was then refluxed for 2 h, ether was added (10 ml) and a white precipitate of succinimide filtered off. The filtrate was evaporated to dryness, and then purified by column chromatography using 5% ether in pentane as eluant to give the title product (604 mg, 79%); 1HNMR (400 MHz, CDCl3) δ: 1.43 (s, 6H), 2.92 (s, 2H), 6.54 (d, 1H), 7.16 (d, 1H), 7.19 (s, 1H); LRMS: M+H, 227. (TS+).

Aufarbeitung

  1. temperatureThe reaction was then refluxed for 2 h
  2. filtrationa white precipitate of succinimide filtered off
  3. customThe filtrate was evaporated to dryness
  4. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4aa208ddefc74a5a9b1404a45bd9e745
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849649B2

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