Azobisisobutyronitrile → Methyl 5-(bromomethyl)-2-fluorobenzoate

HRID 2414372Notes

Reaction equation

HRID 2414372 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1C(=O)N([Br:20])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:12][C:9]1[CH:10]=[CH:11][C:2]([F:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 22645471Methyl 2-fluoro-5-methylbenzoate

Product 1

HCID 22645461Methyl 5-(bromomethyl)-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 2-fluoro-5-methylbenzoate (17.16 g, 102.1 mmol) in CCl4(250 mL) is added NBS (18.2 g, 102.1 mmol) and AIBN (0.83 g, 5.1 mmol), and the resulting solution is refluxed for 3 hours. After cooling, the mixture is filtered through celite, evaporated, and chromatographed (silica, 5 to 15% EtOAc/hexane) to yield methyl 5-bromomethyl-2-fluorobenzoate, as a white solid.

Workup

  1. temperaturethe resulting solution is refluxed for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered through celite
  4. customevaporated
  5. customchromatographed (silica, 5 to 15% EtOAc/hexane)

Sources & evidence

ORD record
ord-d3387d13759347d6b0f119633c712635
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

Loading…