1,3-Dibromopropane → HCID 92135508, Verbindung

HRID 925120

Reaktionsgleichung

Reaktionsgleichung von HRID 925120
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:23][CH2:24][CH2:25]Br>ClCCl.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:16]#[N:17])[CH2:25][CH2:24][CH2:23]2)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 2979634-Benzyloxy-3-methoxyphenylacetonitrile

Produkt 1

HCID 92135508HCID 92135508, VerbindungAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-(benzyloxy)-3-methoxyphenyl)acetonitrile (3.1 g, 12.24 mmol) in dichloromethane (30 mL) was added sodium hydroxide (30 mL, 50% aqueous solution, 367 mmol), TBAB (0.99 g, 3.06 mmol) and then with 1,3-dibromopropane (2 mL, 19.58 mmol). The reaction was stirred at room temperature for 72 hours. The layers were separated, organic layer was dried (MgSO4) and concentrated. Purification by flash chromatography (silica gel, 5-25% EtOAc/hexane) afforded 1-(4-(benzyloxy)-3-methoxyphenyl)cyclobutanecarbonitrile (1.8 g, 50%). MS (ESI) m/z 294 (M+H)+.

Aufarbeitung

  1. customThe layers were separated
  2. dry with materialorganic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by flash chromatography (silica gel, 5-25% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4ba382dbcae64e058b3315ac9ebb5dd1
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284272B2

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