Ammonia → 2-bromo-4-phenylaniline

HRID 735155Notes

Reaction equation

HRID 735155 reaction equation
[BrH:1].[C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.N>CS(C)=O>[Br:1][C:6]1[CH:7]=[C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:3]=[CH:4][C:5]=1[NH2:8]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 71024-Aminobiphenyl

Product 1

HCID 2826272-bromo-4-phenylaniline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

8.7 mL (76.8 mmol) of a 48% hydrogen bromide solution is added dropwise to a solution of 13.008 g (76.8 mmol) of biphenyl-4-ylamine in 60 mL of DMSO at ambient temperature and the mixture is stirred for 14 hours. Then it is heated to 100° C. for 1 hour, the mixture is then cooled and poured onto water. By the addition of ammonia solution, the reaction mixture is made alkaline and the precipitate formed is filtered off and washed with water. The purification is carried out by column chromatography on silica gel (eluant: dichloromethane). Yield: 11.3 g (60% of theory); C12H10BrNO (M=248.19); calc.: molecular ion peak (M+H)+: 248/250 (Cl); found: molecular ion peak (M+H)+: 248/250 (Cl).

Workup

  1. temperaturethe mixture is then cooled
  2. additionpoured onto water
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washwashed with water
  6. customThe purification

Sources & evidence

ORD record
ord-48bf9163e77c4d1289be9f1c025df024
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…