Benzoyl Peroxide → methyl 4-(bromomethyl)-2-fluorobenzoate

HRID 1777531Notes

Reaction equation

HRID 1777531 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18759805Methyl 2-fluoro-4-methylbenzoate

Product 1

HCID 18759821methyl 4-(bromomethyl)-2-fluorobenzoateYield 70.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of methyl 2-fluoro-4-methylbenzoate (0.655 g; 3.89 mmol) in carbon tetrachloride (30 mL) was added N-bromosuccinimide (0.840 g; 4.67 mmol) and benzoyl peroxide (0.097 g; 0.390 mmol). The mixture was refluxed for 18 hours and the resulting suspension was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent 1 to 12% ethyl acetate in heptane) to give 0.676 g (70%) of methyl 4-(bromomethyl)-2-fluorobenzoate as a solid which was directly used in the next step.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. concentrationthe resulting suspension was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel (eluent 1 to 12% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-0b52104ebc9e41ba85b84d7d87ab30bd
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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