Water → Methyl 2-(bromomethyl)-3-fluorobenzoate

HRID 2301126Notes

Reaction equation

HRID 2301126 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH3:11].[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH2:11][Br:13]

Participants

7

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 21752566Methyl 3-fluoro-2-methylbenzoate

Product 1

HCID 19788116Methyl 2-(bromomethyl)-3-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

3-Fluoro-2-methyl-benzoic acid methyl ester (4.3 g, 26 mmol), N-bromosuccinimide (5.0 g, 28 mmol) and AIBN (2,2′-azobisisobutyronitril) (420 mg, 2.6 mmol) were stirred at 80° C. for 10 hours in carbon tetrachloride (45 ml). The reaction solution was mixed with water and chloroform, washed with saturated sodium bicarbonate aqueous solution and saturated brine and then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation from the extract under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 5.1 g (21 mmol, 81% in yield) of the title compound.

Workup

  1. washwashed with saturated sodium bicarbonate aqueous solution and saturated brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customThe solvent was removed by evaporation from the
  4. extractionextract under a reduced pressure
  5. customthe thus obtained material was separated
  6. custompurified by a silica gel column chromatography
  7. customto obtain

Sources & evidence

ORD record
ord-acb67e1114d24c75a6db98c93fadaee7
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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