Dichloromethane → HCID 86071219, Verbindung

HRID 746367

Reaktionsgleichung

Reaktionsgleichung von HRID 746367
[Br:1][CH2:2][C:3](Br)=[O:4].[N+:6]([C:9]1[C:14]([CH2:15][OH:16])=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1)([O-:8])=[O:7].CCN(CC)CC.C(Cl)Cl>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl>[Br:1][CH2:2][C:3]([O:16][CH2:15][C:14]1[CH:13]=[C:12]([O:17][CH3:18])[C:11]([O:19][CH3:20])=[CH:10][C:9]=1[N+:6]([O-:8])=[O:7])=[O:4]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 660976-Nitroveratryl alcohol

Produkt 1

HCID 86071219HCID 86071219, VerbindungAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Bromoacetylbromide (0.19 ml, 2.2 mmol) was slowly added to the solution of 6-nitroveratrylalcohol (0.43 g, 2 mmol), Et3N (0.56 ml, 4 mmol) and DMAP (24 mg, 0.2 mmol) in CHCl3 (5 ml). After stirring at room temperature for five hours, CH2Cl2 (20 ml) was added and the mixture was washed with HCl (1 M, 2×10 ml), NaHCO3 (sat., 10 ml) and water (10 ml). Organic phase was dried over Na2SO4, evaporated and purified by chromatography (Si-gel, CH2Cl2) to yield 4.5-dimethoxy-2-nitrobenzyl 2-bromoacetate (368 mg, 55%).

Aufarbeitung

  1. washthe mixture was washed with HCl (1 M, 2×10 ml), NaHCO3 (sat., 10 ml) and water (10 ml)
  2. dry with materialOrganic phase was dried over Na2SO4
  3. customevaporated
  4. custompurified by chromatography (Si-gel, CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-7be346b8d40a48e3b16b2cdd7e8b52d1
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07393828B2

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