4-Bromoaniline → 1-(4-Bromoanilino)-3-phenyl-2-propanol

HRID 897626

Reaction equation

HRID 897626 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[O:9]1[CH2:18][CH:10]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CO>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:18][CH:10]([OH:9])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 948262-(Phenylmethyl)oxirane

Product 1

HCID 223472001-(4-Bromoanilino)-3-phenyl-2-propanolYield 70.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-bromoaniline (1.75 g, 0.0102 mol) and 2,3-epoxy-propylbenzene (1.77 g, 0.0132 mol) in methanol (40 mL) was heated at reflux for 16 hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was purified by flash chromatography on silica using ethyl acetate/n-heptane (1:5) as mobile phase to yield 1-(4-bromoanilino)-3-phenyl-2-propanol (2.2 g, 0.00719 mol) as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-a1d99133df9c49e5934ae015ef333b4c
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Linked notes

Loading…