Benzoyl Peroxide → 1-(Bromomethyl)-4-fluoro-2-iodobenzene

HRID 2252798Notes

Reaction equation

HRID 2252798 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([I:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[I:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 832204-Fluoro-2-iodotoluene

Product 1

HCID 128060541-(Bromomethyl)-4-fluoro-2-iodobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 4-fluoro-2-iodotoluene (14.3 g, 60.6 mmol, Lancaster Synthesis), N-bromosuccinimide (16.2 g, 90.9 mmol), and benzoyl peroxide (0.74 g, 3.0 mmol) in carbon tetrachloride (500 mL) was heated to reflux for 3 days. Additional NBS (0.5 eq portions) was added as needed over this period to drive the reaction to completion. The reaction was cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (ISCO column, 110 g silica gel) eluting with 100% hexane to afford the desired product as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 days
  3. waitas needed over this period
  4. customthe reaction to completion
  5. temperatureThe reaction was cooled
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was purified by flash column chromatography (ISCO column, 110 g silica gel)
  9. washeluting with 100% hexane

Sources & evidence

ORD record
ord-e5df85483fd4471390e0f3486fa485b3
Source dataset
uspto-grants-2008_01
Patent number
US07323460B2

Reaction notes

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