Azobisisobutyronitrile → HCID 20711242, compound

HRID 661058Notes

Reaction equation

HRID 661058 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-0bc8588d6ede4383afb217f87c68618c
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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