Benzoyl Peroxide → 1-Bromo-4-(bromomethyl)-2-fluorobenzene

HRID 2246767Notes

Reaction equation

HRID 2246767 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:28]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:28])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5732804-Bromo-3-fluorotoluene

Product 1

HCID 116661761-Bromo-4-(bromomethyl)-2-fluorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a room temperature solution of 4-bromo-3-fluorotoluene (10.6 g) in 150 mL of carbon tetrachloride were added benzoyl peroxide (100 mg) and N-bromosuccinimide (10 g). The mixture was heated at 80° C. (with shine light) for 4 hours. The reaction mixture was cooled to 0° C. Filtered through celite, washed with hexanes and the solvent removed in vacuo. The crude material was purified by chromatography on SiO2 using hexanes to yield the title compound containing ˜30% of 1-bromo-4-(dibromomethyl)-2-fluorobenzene as impurity.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C
  2. filtrationFiltered through celite
  3. washwashed with hexanes
  4. customthe solvent removed in vacuo
  5. customThe crude material was purified by chromatography on SiO2

Sources & evidence

ORD record
ord-6378265c2e4a4a588aa5dd94f68a73dd
Source dataset
uspto-grants-2010_03
Patent number
US07687524B2

Reaction notes

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