Benzoyl Peroxide → Ethyl 2-(bromomethyl)-4-[4-(difluoromethyl)phenoxy]-1-benzofuran-6-carboxylate

HRID 1177291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177291
[F:1][CH:2]([F:25])[C:3]1[CH:24]=[CH:23][C:6]([O:7][C:8]2[C:13]3[CH:14]=[C:15]([CH3:17])[O:16][C:12]=3[CH:11]=[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:9]=2)=[CH:5][CH:4]=1.C1C(=O)N([Br:33])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:33][CH2:17][C:15]1[O:16][C:12]2[CH:11]=[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:9]=[C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([CH:2]([F:1])[F:25])=[CH:24][CH:23]=3)[C:13]=2[CH:14]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 59559977Ethyl 4-[4-(difluoromethyl)phenoxy]-2-methyl-1-benzofuran-6-carboxylate

Produkt 1

HCID 59560246Ethyl 2-(bromomethyl)-4-[4-(difluoromethyl)phenoxy]-1-benzofuran-6-carboxylateAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-[4-(difluoromethyl)phenoxy]-2-methyl-1-benzofuran-6-carboxylate (710 mg, 2.05 mmol) and NBS (438 mg, 2.46 mmol) in CHCl3 (25 mL) was added benzoyl peroxide (49.7 mg, 0.205 mmol). The mixture was refluxed for 14 hours. The solvent was evaporated, and the product was purified via gradient silica gel chromatography using hexanes/EtOAc (100/0 to 70/30) to give the title compound (440 mg, 51%) as a light-yellow solid. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.38 (t, J=7.16 Hz, 3 H) 4.38 (q, J=7.16 Hz, 2 H) 4.53 (s, 2 H) 6.39-6.89 (m, 2 H) 7.07 (d, J=8.48 Hz, 2 H) 7.49 (d, J=8.48 Hz, 2 H) 7.54 (d, J=0.94 Hz, 1 H) 8.01 (s, 1 H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 14 hours
  2. customThe solvent was evaporated
  3. customthe product was purified via gradient silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e122d2398e3c4d30a9b3c3c4987bd670
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842713B2

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