Benzoyl Peroxide → Methyl 3,5-dibromo-4-(bromomethyl)benzoate

HRID 394078Notes

Reaction equation

HRID 394078 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([Br:1])[C:11]([CH2:12][Br:14])=[C:10]([Br:13])[CH:9]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 624016Methyl 3,5-dibromo-4-methylbenzoate

Product 1

HCID 22647948Methyl 3,5-dibromo-4-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 3,5-dibromo-4-methylbenzoate (150.0 g, 0.487 mol) in 2 L anhydrous CCl4 under a nitrogen atmosphere was added N-bromosuccinimide (125.7 g, 0.706 mol) and benzoyl peroxide (12.98 g, 0.054 mol). The solution was then heated to reflux. Once the solution reached reflux it was irradiated with a 250 W sun lamp. After 6 h the solution was cooled to RT and filtered. The precipitate (succinimde) was washed with DCM and the filtrate concentrated. The residue (ca. 246 g) was purified by silica gel chromatography (3 Kg SiO2) using 5 to 25% DCM/hexanes as the eluent to give methyl-4-bromomethyl-3,5-dibromo-benzoate. 1H NMR(CDCl3, 500 MHz): δ 3.93 (s, 3H), 4.84 (s, 2H), 8.21 (s, 2H). MS(ES) 385 (M+1); LC 1: 3.93 min.

Workup

  1. temperatureThe solution was then heated to reflux
  2. temperatureOnce the solution reached reflux it
  3. customwas irradiated with a 250 W sun lamp
  4. filtrationfiltered
  5. washThe precipitate (succinimde) was washed with DCM
  6. concentrationthe filtrate concentrated
  7. customThe residue (ca. 246 g) was purified by silica gel chromatography (3 Kg SiO2)

Sources & evidence

ORD record
ord-6c4aa05629344320bdb24bf6d46c8f95
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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