Benzyl Alcohol → Benzyl 4-bromomethyl-3-nitrobenzoate

HRID 1360785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360785
[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-e5fed4e5f6894d88916631b13015d59d
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879850B2

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