Hydrochloric Acid → 3-Bromo-4-isopropylaniline hydrochloride

HRID 59585Notes

Reaction equation

HRID 59585 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH:11]([CH3:13])[CH3:12].[ClH:14]>O>[ClH:14].[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH:11]([CH3:13])[CH3:12])[NH2:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 215316212-Bromo-4-nitro-1-(propan-2-yl)benzene

Product 1

HCID 898762743-Bromo-4-isopropylaniline hydrochlorideYield 99.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Bromo-1-isopropyl-4-nitrobenzene (XI) (50 g, 0.192 mol, 93.5 GC-% by area), 100 ml of water, ironpowder (40.71 g, 0.718 mol) were heated to 70° C. and hydrochloric acid (193.7 g, 1.647 mol, 31% in water) was added over a period of 2 hours. The mixture was then cooled to 0° C. and the suspension was filtered with suction. The solvent obtained was dried overnight at 50° C. in a vacuum drying oven. 3-Bromo-4-isopropylaniline hydrochloride (48 g, purity: 88.7%, contains: 8.6% of iron, 88.7% of theory) was obtained as a light-brown solid.

Workup

  1. filtrationthe suspension was filtered with suction
  2. customThe solvent obtained
  3. customwas dried overnight at 50° C. in a vacuum
  4. customdrying oven

Sources & evidence

ORD record
ord-8621d3ae4f5b483a90c40474d49db0e0
Source dataset
uspto-grants-2016_09
Patent number
US09440908B2

Reaction notes

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