4-Bromoaniline → 2-[(4-bromophenyl)amino]ethan-1-ol

HRID 1061598Notes

Reaction equation

HRID 1061598 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br[CH:10]([OH:12])[CH3:11].[OH-].[Na+]>>[OH:12][CH2:10][CH2:11][NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 14798Sodium HydroxideHCID 14202443Ethanol, 1-bromo-

Product 1

HCID 126977882-[(4-bromophenyl)amino]ethan-1-ol

Conditions

Temperature
70 °C

Procedure

A mixture of p-bromoaniline (17.2 g, 100 m mol) and bromoethanol (3.54 mL, 50 m mol) in a 50 mL round bottle was heated gradually to 70° C. and then was stirred at 70° C. overnight. The reaction mixture was then cooled, basified with aq. NaOH, and extracted with ether. The ether layers were dried over Na2SO4 and concentrated to near dryness. N-β-hydroxyethyl-p-bromoaniline was obtained as a crystalline material (5.1 g, 47%). 1H NMR (CDCl3): δ 7.28 (2H, d, J=8.8 Hz), 6.60 (2H, d, J=8.8 Hz), 3.86 (2H, t, J=5.1 Hz), 3.29 (2H, t, J=5.1 Hz), 3.00 (2H, br s) ppm.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with ether
  3. dry with materialThe ether layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8c54dd3edca94b32a28c9cbfbecdb23f
Source dataset
uspto-grants-2005_11
Patent number
US06960595B2

Reaction notes

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