Azobisisobutyronitrile → HCID 20711242, compound

HRID 2109731Notes

Reaction equation

HRID 2109731 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:15][CH:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 11241070Ethyl 2-(3,4-difluorophenyl)acetate

Product 1

HCID 20711242HCID 20711242, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl 2-(3,4-difluorophenyl)acetate (1.20 g, 5.99 mmol), N-bromosuccinimide (1.17 g, 6.59 mmol), and 2,2′-azobis(isobutyronitrile) (0.148 g, 0.899 mmol) in CCl4 (20 mL) was gradually heated to reflux and stirred at this temperature overnight. The solvent was removed in vacuum. The residue was purified by flash column chromatography (100% hexanes for 5 minutes, then 0 to 5% of EtOAc in hexanes over 23 minutes). The desired product was obtained as a colorless oil (1.14 g, 68%). 1H NMR (300 MHz, CDCl3) δ 1.31 (d, J=6.0 Hz, 3H), 4.17-4.35 (m, 2H), 5.27 (s, 1H), 7.11-7.20 (m, 1H), 7.24-7.30 (m, 1H), 7.42-7.52 (m, 1H).

Workup

  1. temperaturewas gradually heated
  2. temperatureto reflux
  3. customThe solvent was removed in vacuum
  4. customThe residue was purified by flash column chromatography (100% hexanes for 5 minutes
  5. wait0 to 5% of EtOAc in hexanes over 23 minutes)

Sources & evidence

ORD record
ord-454728e1eac648a59cb985a3cdf28ec3
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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