Water → 5-(Bromomethyl)-2-fluorobenzonitrile

HRID 1627250Notes

Reaction equation

HRID 1627250 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5].[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:10][C:7]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27745842-Fluoro-5-methylbenzonitrile

Product 1

HCID 27739315-(Bromomethyl)-2-fluorobenzonitrileYield 33.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-fluoro-5-methylbenzonitrile (3.00 g, 22 mmol), N-bromosuccinimide (4.12 g, 23 mmol) and benzoyl peroxide (1.07 g, 4.4 mmol) in CCl4 (100 mL) was heated at reflux 6 h. The reaction mixture was cooled to room temperature and then combined with water. The separated organic phase was dried over MgSO4, filtered through a Celite™ pad, and evaporated under reduced pressure. Purification by flash chromatography (Hex/EtOAc, 20:1) gave 5-(bromomethyl)-2-fluorobenzonitrile (1.58 g, 33% yield) as an oil. 1H NMR (CDCl3, 400 MHz): δ 4.45 (s, 2H), 7.21 (m, 1H), 7.65 (m, 2H).

Workup

  1. temperatureat reflux 6 h
  2. dry with materialThe separated organic phase was dried over MgSO4
  3. filtrationfiltered through a Celite™ pad
  4. customevaporated under reduced pressure
  5. customPurification by flash chromatography (Hex/EtOAc, 20:1)

Sources & evidence

ORD record
ord-3df850d2a6d04bf8bbda0420d070fd5e
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

Loading…