Azobisisobutyronitrile → HCID 58009419, compound

HRID 1009470Notes

Reaction equation

HRID 1009470 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[CH3:13].[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[F:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18920169HCID 18920169, compound

Product 1

HCID 58009419HCID 58009419, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3.00 g of ethyl 4-fluoro-3-methylbenzoate was dissolved in 50.0 mL of carbon tetrachloride, and 4.40 g of N-bromosuccinimide and 1.35 g of 2,2′-azobisisobutyronitrile were added thereto, followed by heating under reflux for 4 hours. The reaction liquid was cooled to room temperature, and then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) to obtain 1.73 g of ethyl 3-(bromomethyl)-4-fluorobenzoate.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. customThe reaction liquid
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-6eb69853ecdd41388610164f0c120782
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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