Bromine → HCID 22028546, compound

HRID 1829147Notes

Reaction equation

HRID 1829147 reaction equation
[CH:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Br:12]Br>C(O)(=O)C>[Br:12][C:10]1[CH:11]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

4

Reactant 2

HCID 24408BromineHCID 821124-Isopropoxyaniline

Product 1

HCID 22028546HCID 22028546, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

4-Isopropoxyaniline (24.2 g) was dissolved in acetic acid (300 mL), and a mixture of bromine (8.25 mL) and acetic acid (80 mL) was added dropwise. After stirring at room temperature for 2 hr, the reaction mixture was concentrated under reduced pressure. Water was added to residue, and the mixture was extracted with diethylether. The extract was washed successively with aqueous sodium thiosulfate solution and brine, is and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 2-bromo-4-isopropoxyaniline (10.2 g) as a black brown oil.

Workup

  1. additionwas added dropwise
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to residue
  4. extractionthe mixture was extracted with diethylether
  5. washThe extract was washed successively with aqueous sodium thiosulfate solution and brine
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c01dd4fcbacb4a3dadda7d70200a34a8
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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