Benzoyl Peroxide → 2-(Bromomethyl)-6-fluoronaphthalene

HRID 989621Notes

Reaction equation

HRID 989621 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.C1C(=O)N([Br:20])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27278452-Fluoro-6-methylnaphthalene

Product 1

HCID 5946332-(Bromomethyl)-6-fluoronaphthalene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

6-Fluoro-2-methylnaphthalene (20.5 g, 128 mmol, prepared by adaptation of the method of Wolinska-Mocydlarz et al2) and NBS (22.8 g, 128 mmol) were heated at reflux for 16 hr in CCl4 (210 mL) during which time, benzoyl peroxide (2.5 g) was added portionwise. The cooled solution was filtered and evaporated and the residue was extracted thoroughly with hexane (4×250 mL). The extracts were decanted from tarry material, combined and evaporated to give the product as a yellow solid, 29.8 g (97%).

Workup

  1. temperaturewere heated
  2. additionwas added portionwise
  3. filtrationThe cooled solution was filtered
  4. customevaporated
  5. extractionthe residue was extracted thoroughly with hexane (4×250 mL)
  6. customThe extracts were decanted from tarry material
  7. customevaporated

Sources & evidence

ORD record
ord-5cd8038720464ff5a4fabe12d3de951b
Source dataset
uspto-grants-2002_10
Patent number
US06458779B1

Reaction notes

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