Azobisisobutyronitrile → HCID 19002062, compound

HRID 659973Notes

Reaction equation

HRID 659973 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[Cl:30]C1C=CC=CC=1>>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][Cl:30])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7964ChlorobenzeneHCID 67184N-bromobutanimideHCID 135375362-Bromo-3-fluoro-5-methylpyridine

Product 1

HCID 19002062HCID 19002062, compoundYield 42%

Procedure

10.00 g (52.63 mmol) of 6-bromo-5-fluoro-3-methylpyridin (cf. F. L. Setliff, Organic Preparations and Procedures International 1971, 3, 217-222), 12.18 g (68.42 mmol) of N-bromosuccinimide and 0.86 g (5.26 mmol) of 2,2′-azobis(2-methylpropanenitrile) in 1 of chlorobenzene are boiled under reflux for 6 hours. The reaction mixture is washed with saturated aqueous sodium sulphite solution and sodium bicarbonate solution and then dried over sodium sulphate and concentrated under reduced pressure. Column chromatography of the residue on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (1:20) gives 6.0 g (42% of theory) of 6-bromo-3-chloromethyl-5-fluoropyridine.

Workup

  1. temperatureunder reflux for 6 hours
  2. washThe reaction mixture is washed with saturated aqueous sodium sulphite solution and sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ea0a83ae11d4adb96514fc7d50c9ff2
Source dataset
uspto-grants-2011_12
Patent number
US08084452B2

Reaction notes

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