Ethanol → (2-Amino-4-bromophenyl)methanol

HRID 1360307

Reaktionsgleichung

Reaktionsgleichung von HRID 1360307
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:10][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[CH2:8][OH:9]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 15906236(4-Bromo-2-nitrophenyl)methanol

Produkt 1

HCID 53440895(2-Amino-4-bromophenyl)methanolAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of (4-bromo-2-nitro-phenyl)-methanol (1.85 g, 7.97 mmol), iron powder (2.23 g, 39.9 mmol), ammonium chloride (213 mg, 3.99 mmol), ethanol (20 mL), and water (10 mL) was heated at 75° C. for 1 h, then after cooling filtered through a pad of diatomaceous earth. The filtrate was evaporated and the residue partitioned between ethyl acetate and water, the organic layer was washed with brine, dried (MgSO4), and evaporated to produce (2-amino-4-bromo-phenyl)-methanol (1.53 g, 90%). Off-white solid, MS (EI)=201.0 (M+).

Aufarbeitung

  1. temperatureafter cooling
  2. filtrationfiltered through a pad of diatomaceous earth
  3. customThe filtrate was evaporated
  4. customthe residue partitioned between ethyl acetate and water
  5. washthe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-750b8360f5894fb8a77b7e6101fc8346
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879845B2

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