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

HRID 432338

Reaction equation

HRID 432338 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-dc01332db9424d8487704a15843dc794
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Linked notes

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