N-bromobutanimide → 5-Bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene

HRID 1880431

Reaction equation

HRID 1880431 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([F:9])=[C:4]([CH2:10][Br:11])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27362985-Bromo-2-fluoro-1,3-dimethylbenzene

Product 1

HCID 669206545-Bromo-1-(bromomethyl)-2-fluoro-3-methylbenzeneYield 100.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 5-bromo-2-fluoro-1,3-dimethylbenzene (5.0 g, 25 mmol) in carbon tetrachloride (100.0 mL) was added N-bromosuccinimide (4.11 g, 23.1 mmol) and benzoyl peroxide (100.0 mg, 0.017 mmol). The reaction was heated at reflux for 7 hours. The reaction was filtered and the filtrate washed with 2N HCl, saturated aqueous sodium bicarbonate, water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was flash chromatographed (5% EtoAc/Haptanes) to obtain 6.56 g of 5-bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene as an oil product. 1H NMR (400 MHz, CDCl3) δ ppm 2.22-2.36 (s, 3 H) 4.42 (d, J=0.98 Hz, 2 H) 7.21-7.37 (m, 2 H)

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 7 hours
  3. filtrationThe reaction was filtered
  4. washthe filtrate washed with 2N HCl, saturated aqueous sodium bicarbonate, water and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (5% EtoAc/Haptanes)

Sources & evidence

ORD record
ord-4b345bc30f60488db40c42acdba3cf03
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Linked notes

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