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

HRID 8394Notes

Reaction equation

HRID 8394 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 (NBS, 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-8b373ac0387f4214a1526b9b4b83818b
Source dataset
uspto-grants-2006_08
Patent number
US07087765B2

Reaction notes

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