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

HRID 916230Notes

Reaction equation

HRID 916230 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-27a15b679fa8412b88ca965947944375
Source dataset
uspto-grants-2007_09
Patent number
US07268166B2

Reaction notes

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