Carbon tetrabromide → 2-(Bromomethyl)-1-benzofuran

HRID 29462

Reaktionsgleichung

Reaktionsgleichung von HRID 29462
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10]O.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:13][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 27762631-Benzofuran-2-Ylmethanol

Produkt 1

HCID 123263162-(Bromomethyl)-1-benzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To benzofuran-2-yl-methanol (4.3 g, 29.0 mmol, 1 eq., Example 140, Step 1), dichloromethane (200 mL) was added and the solution was cooled using an ice-ethanol bath. Then carbon tetrabromide (10.6 g, 31.9 mmol, 1.1 eq.) and 1,3-bis(diphenylphosphino)-propane (6.6 g, 16.0 mmol, 0.55 eq.) were added under argon, and the reaction was allowed to slowly warm to room temperature for 2.5 hours. After work-up and flash column chromatography, 2-bromomethyl-benzofuran was obtained in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.9 (s, 2 H) 7.0 (dd, J=5.3, 0.5 Hz, 1 H) 7.3 (dd, 1 H) 7.4 (m, 1 H) 7.6 (m, 2 H).

Aufarbeitung

  1. temperaturethe solution was cooled

Quellen und Nachweise

ORD-Eintrag
ord-5e37f8f94d1b426cad88bcdac50e03f6
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420001B2

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