Benzoyl Peroxide → Methyl 4-(bromomethyl)-3-fluorobenzoate

HRID 1777535Notes

Reaction equation

HRID 1777535 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[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:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18973767Methyl 3-fluoro-4-methylbenzoate

Product 1

HCID 18766370Methyl 4-(bromomethyl)-3-fluorobenzoateYield 48%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of methyl 3-fluoro-4-methylbenzoate (0.630 g; 3.75 mmol) in carbon tetrachloride (30 mL) was added N-bromosuccinimide (0.840 g, 4.67 mmol) and benzoyl peroxide (0.094 g; 0.375 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 0.444 g (48%) of methyl 4-(bromomethyl)-3-fluorobenzoate as an oily residue 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-364f6dd1544344c1aaf7ec2f7fdebfd4
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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