4-Acetamido-3-bromoacetophenone → 1-(4-Amino-3-bromo-phenyl)-ethanone

HRID 1098760Notes

Reaction equation

HRID 1098760 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10]C(=O)C)=[C:6]([Br:14])[CH:5]=1)(=[O:3])[CH3:2]>Cl>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][C:6]=1[Br:14]

Participants

3

Reactant 1

HCID 36824744-Acetamido-3-bromoacetophenone

Product 1

HCID 15152811-(4-Amino-3-bromo-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(4-Acetyl-2-bromo-phenyl)-acetamide (10.0 g, 39.05 mmol) in concentrated hydrochloric acid (200 mL) was stirred for 5 h under reflux. The reaction mixture was concentrated under reduced pressure. The residue was treated with a saturated aqueous solution of NaHCO3 (75 mL), extracted with CH2Cl2 (2×70 mL) and dried over Na2SO4. Evaporation leads to the product (8.35 g, 100%) which was used in step 2 without further purification.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was treated with a saturated aqueous solution of NaHCO3 (75 mL)
  4. extractionextracted with CH2Cl2 (2×70 mL)
  5. dry with materialdried over Na2SO4
  6. customEvaporation
  7. customwas used in step 2 without further purification

Sources & evidence

ORD record
ord-b0138cc4b3474d00af8ea8ffcd007ca8
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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