N-bromobutanimide → 3-Bromo-5-(bromomethyl)benzonitrile

HRID 564466Notes

Reaction equation

HRID 564466 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[C:5]#[N:6].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH2:10][Br:18])[CH:9]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 145678583-Bromo-5-methylbenzonitrile

Product 1

HCID 145678613-Bromo-5-(bromomethyl)benzonitrileYield 101%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-bromo-5-methylbenzonitrile (9.80 g, 45.0 mmol), NBS (8.90 g, 45.0 mmol) and BPO (0.40 g) in CCl4 (250 mL) was heated for 10 h at reflux. The reaction mixture was cooled to room temperature and filtered, and the organic phase was washed successively with saturated sodium bicarbonate (100 mL), water (2×50 mL) and brine (2×50 mL). The combined organic phases were dried over Na2SO4 and concentrated in vacuum to give 12.5 g of crude 3-bromo-5-(bromomethyl)benzonitrile.

Workup

  1. temperaturewas heated for 10 h
  2. temperatureat reflux
  3. filtrationfiltered
  4. washthe organic phase was washed successively with saturated sodium bicarbonate (100 mL), water (2×50 mL) and brine (2×50 mL)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-9d4d547c907342558f7ec0fe52e79b48
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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