Water → HCID 86699741, Verbindung

HRID 515172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515172
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][C:12]=2[O:24]C)=[CH:4][CH:3]=1.B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:13][C:12]=2[OH:24])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 25134Boron tribromideHCID 86699740HCID 86699740, Verbindung

Produkt 1

HCID 86699741HCID 86699741, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-[(4-fluorophenyl)-methyl]-2-methoxy-6-methyl-4-morpholin-4-yl-benzamide (2.50 g, 6.98 mmol) in dichloromethane (70 ml) is added neat boron tribromide (0.99 ml, 10.3 mmol) at −78° C. The temperature is slowly raised to RT over a period of 30 min and stirred for 1 h at RT. The reaction mixture is poured onto cold water and extracted with dichloromethane (3×50 ml). The combined organic layers are washed with brine (30 ml), dried over sodium sulfate and evaporated to dryness. The crude material is purified by column chromatography (silica gel, 25% ethyl acetate/hexane) affording N-[(4-fluorophenyl)-methyl]-2-hydroxy-6-methyl-4-morpholin-4-yl-benzamide (0.90 g, 2.58 mmol, 37%).

Aufarbeitung

  1. extractionextracted with dichloromethane (3×50 ml)
  2. washThe combined organic layers are washed with brine (30 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude material is purified by column chromatography (silica gel, 25% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-104f886d44a14916adfddc1c24de3f7a
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108936B2

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