Bromine → HCID 44512476, compound

HRID 536338Notes

Reaction equation

HRID 536338 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:13])=[C:7]([NH:9][C:10](=[O:12])[CH3:11])[CH:8]=1.[Br:14]Br>C(O)(=O)C>[Br:14][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([NH:9][C:10](=[O:12])[CH3:11])=[C:6]([CH3:13])[CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 231720n-(5-methoxy-2-methylphenyl)acetamide

Product 1

HCID 44512476HCID 44512476, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-(5-methoxy-2-methylphenyl)acetamide in acetic acid (40 mL) was added Br2 (3 g, 19 mmol) slowly. The mixture was capped and stirred at 50° C. for 5 hours. The reaction was cooled to room temperature, then quenched with sodium sulfite aqueous solution, and extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over Na2SO4 and concentrated to give crude N-(4-bromo-5-methoxy-2-methylphenyl)acetamide as a brown oil, which was used in the next step without further purification.

Workup

  1. customThe mixture was capped
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with sodium sulfite aqueous solution
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-96417e96e1eb469a852db45b07a0aceb
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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