Azobisisobutyronitrile → 5-(Bromomethyl)-4-(4-chlorophenyl)-2-fluoropyridine

HRID 1518842Notes

Reaction equation

HRID 1518842 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[CH:12][N:11]=[C:10]([F:15])[CH:9]=2)=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:14][C:13]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:9][C:10]([F:15])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 672259184-(4-Chlorophenyl)-2-fluoro-5-methylpyridine

Product 1

HCID 672273415-(Bromomethyl)-4-(4-chlorophenyl)-2-fluoropyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of EXAMPLE 307A (1.2 g), N-bromosuccinimide (1.06 g) and AIBN (azobisisobutyronitrile) (0.178 g) in CCl4 (30 mL) was heated under reflux for 6 hours. After cooling, the solid was filtered off. The filtrate was concentrated and loaded onto a silica gel column eluting with 3% ethyl acetate in hexanes to give the title compound.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureAfter cooling
  3. filtrationthe solid was filtered off
  4. concentrationThe filtrate was concentrated
  5. washeluting with 3% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5cc2694fe2fb4542b0c48261b415969c
Source dataset
uspto-grants-2015_07
Patent number
US09072748B2

Reaction notes

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