N-bromobutanimide → 2-(Bromomethyl)-5-fluorobenzonitrile

HRID 322562Notes

Reaction equation

HRID 322562 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[Br:11]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:10][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:9][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 5226685-Fluoro-2-methylbenzonitrile

Product 1

HCID 220157702-(Bromomethyl)-5-fluorobenzonitrileYield 102%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-fluoro-2-methylbenzonitrile (10.0 g, 74.0 mmol), N-bromosuccinimide (NMS, 13.2 g, 74.0 mmol), benzoyl peroxide (0.2 g, 0.82 mmol), and carbon tetrachloride (100 mL) was refluxed for 18 h. The reaction mixture was then cooled to room temperature and filtered through fritted glass. The solid in the funnel was washed with carbon tetrachloride (3×50 mL) and evaporated to dryness under vacuum to provide 16.1 g, 102% yield of product.

Workup

  1. temperaturewas refluxed for 18 h
  2. filtrationfiltered through fritted glass
  3. washThe solid in the funnel was washed with carbon tetrachloride (3×50 mL)
  4. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-8a85bffe9d414d689a276bf274601bbe
Source dataset
uspto-grants-2001_04
Patent number
US06211245B1

Reaction notes

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