N-bromobutanimide → 4-Bromo-2-fluorobenzyl bromide

HRID 1078032Notes

Reaction equation

HRID 1078032 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([F:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:10])=[C:4]([F:9])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1710404-Bromo-2-fluorotoluene

Product 1

HCID 27336604-Bromo-2-fluorobenzyl bromideYield 94.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

1-Bromo-3-fluoro-4-methylbenzene (28.37 g, 0.15 mol, 1 eq), N-bromosuccinimide (26.72 g, 0.15 mol, 1 eq), azobisisobutyronitrile (1.44 g) and carbon tetrachloride (500 mL) were mixed and refluxed overnight. The mixture was filtered and washed with water (3×300 mL). The organic layer was dried (MgSO4), and the solvent removed in vacuo to yield 37.88 g of an oil (75% product by NMR). NMR (CDCl3) δ 4.45 (s, 2H). This material was used in the subsequent step without further purification. ##STR47##

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe mixture was filtered
  3. washwashed with water (3×300 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8c7722b584694664962d8c70ab4fa39e
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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