Acetic Acid → HCID 86703920, compound

HRID 1049918Notes

Reaction equation

HRID 1049918 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].CC(O)=O.[O:14]1[CH2:17][C:16](=O)[CH2:15]1.O>CCO>[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[N:5]=[C:16]1[CH2:17][O:14][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 150201553-Bromo-5-fluoroanilineHCID 150242543-Oxetanone

Product 1

HCID 86703920HCID 86703920, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-bromo-5-fluoroaniline (CAS 134168-97-1) (3.0 g, 16 mmol) in EtOH (50 mL), was added HOAc (900 mg, 16 mmol), and oxetan-3-one (CAS 6704-31-0) (2.4 g, 32 mmol). The mixture was stirred at reflux for overnight. It was poured into water (100 mL) and extract with EtOAc (100 mL×2). The combined organic layers was dried over Na2SO4 and concentrated in vacuum to give the crude product (3.0 g, 77%).

Workup

  1. temperatureat reflux for overnight
  2. extractionextract with EtOAc (100 mL×2)
  3. dry with materialThe combined organic layers was dried over Na2SO4
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-5c4bea3ce21f4aea9aa51e2194fc44bc
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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