Azobisisobutyronitrile → 3-(Bromomethyl)-2-fluorobenzoic acid

HRID 1012108Notes

Reaction equation

HRID 1012108 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:10]1[C:2]([F:1])=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27373792-Fluoro-3-methylbenzoic acid

Product 1

HCID 190422703-(Bromomethyl)-2-fluorobenzoic acidYield 17.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-fluoro-3-methylbenzoic acid (0.462 g, 3 mmol), N-bromosuccinimide (0.560 g, 3.15 mmol), azobisisobutyronitrile (AIBN) (0.024 g, 0.15 mmol) and CCl4 (10 ml) was heated at reflux for 18 h. The reaction mixture was then reduced in vacuo and partitioned between ethyl acetate and aqueous K2CO3. The aqueous layer was acidified (2M HCl) and cooled in ice. The precipitate obtained was collected by filtration and dried in vacuo to give 3-bromomethyl-2-fluoro-benzoic acid (0.1225 g, 13%) as a colourless solid. (LC/MS: Rt 3.18, [M−H]− 232.91).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. custompartitioned between ethyl acetate and aqueous K2CO3
  4. temperaturecooled in ice
  5. customThe precipitate obtained
  6. filtrationwas collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-544a0d8953064465ad30eb1a7caabb66
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

Loading…