Benzyl Alcohol → Benzyl 4-bromomethyl-3-nitrobenzoate

HRID 1513281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513281
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[CH2:15](O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:15]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][Br:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 1323864-Bromomethyl-3-nitrobenzoic acid

Produkt 1

HCID 66965750Benzyl 4-bromomethyl-3-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-bromomethyl-3-nitrobenzoic acid (2.0 g, 7.69 mmol), benzyl alcohol (796 □L, 832 mg, 7.69 mmol) and 4-dimethylaminopyridine (9.4 mg, 77 μmol) in dichloromethane (5 mL) was added DCC (1.59 g, 7.71 mmol) and the mixture was at stirred RT for 3 h. The mixture was filtered and the filtrate concentrated. The residue was purified by chromatography using a 0-30% gradient of heptane/ethyl acetate to give the title compound as an oil.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-016b6aec724f44acbb4870164b93daa8
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217065B2

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