Azobisisobutyronitrile → HCID 86681288, compound

HRID 1467348Notes

Reaction equation

HRID 1467348 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11].C1C(=O)N([Br:21])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:21][CH:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimide2×HCID 67995851HCID 67995851, compound

Product 1

HCID 86681288HCID 86681288, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 2,6-difluorophenylacetate (2.141 g, 11.50 mmol), NBS (2.6 g, 14.61 mmol) and AIBN (0.057 g, 0.345 mmol) were taken up in CCl4 (45 mL). The reaction mixture was stirred at reflux for 18 hours. Additional NBS (1.433 g, 8.05 mmol) and AIBN (0.038 g, 0.230 mmol) were added and stirring at reflux continued for 24 hours. Room temperature was attained and the reaction mixture filtered through Celite, washing with DCM. The filtrate was concentrated in vacuo and the residue purified by MPLC (0-10% EtOAc-hexanes) to give methyl bromo(2,6-difluorophenyl)-acetate as a pale yellow oil.

Workup

  1. temperatureat reflux for 18 hours
  2. stirringstirring
  3. temperatureat reflux
  4. customRoom temperature
  5. filtrationthe reaction mixture filtered through Celite
  6. washwashing with DCM
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue purified by MPLC (0-10% EtOAc-hexanes)

Sources & evidence

ORD record
ord-6b56df49a3814a5bada79752d68bd039
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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