N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamide → 1-(4-Amino-2,6-dimethylphenyl)-2-bromoethanone

HRID 1465511Notes

Reaction equation

HRID 1465511 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([NH:12]C(=O)C)=[CH:7][C:6]=1[CH3:16])=[O:4]>C(O)C.Cl>[NH2:12][C:8]1[CH:7]=[C:6]([CH3:16])[C:5]([C:3](=[O:4])[CH2:2][Br:1])=[C:10]([CH3:11])[CH:9]=1

Participants

4

Reactant 1

HCID 18788447N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamide

Product 1

HCID 866908101-(4-Amino-2,6-dimethylphenyl)-2-bromoethanoneYield 85.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamide (1-1, 6.92 g, 24.4 mmol) in 20.0 mL of ethanol and 10.2 mL of concentrated hydrochloric acid was heated at reflux for 1.5 h. The solution was concentrated and added with ethyl acetate (100 mL) and saturated aqueous Na2CO3 (100 mL). The organic layer was collected, dried over anhydrous MgSO4(s), and concentrated under reduced pressure to give 1-(4-amino-2,6-dimethylphenyl)-2-bromoethanone (1-2, 5.04 g) as yellow solids, which was used directly for the next step without further purification.

Workup

  1. temperatureat reflux for 1.5 h
  2. concentrationThe solution was concentrated
  3. additionadded with ethyl acetate (100 mL) and saturated aqueous Na2CO3 (100 mL)
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous MgSO4(s)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb240e2b7a92465f9bbc0a606540974a
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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