Benzoyl Peroxide → 4-Bromomethyl-2-fluoropyridine

HRID 426113Notes

Reaction equation

HRID 426113 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.[W]>[Br:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27374032-Fluoro-4-methylpyridine

Product 1

HCID 139851684-Bromomethyl-2-fluoropyridineYield 28.4%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture of 2-Fluoro-4-methyl-pyridine (10 g, 90 mmol), N-bromosuccinimide (19.2 g, 108 mmol), and benzoyl peroxide (2.18 g, 9 mmol) in carbon tetrachloride (100 ml) was refluxed for 5 hr under a light of 500 W tungsten light. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo to give a brown oil, which was purified by silica gel column chromatography (eluent, ether:hexane (1:9)) to afford 4.85 g (28%) of a pale brown oil; 1H NMR (200 MHz, CDCl3) δ: 4.40 (2H, s), 6.95 (1H, m), 7.19 (1H, m), 8.18 (1H, d, J=5.2 Hz); m/z (EI): 189 (M+), 191 (M+2+).

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customto give a brown oil, which
  4. customwas purified by silica gel column chromatography (eluent, ether:hexane (1:9))

Sources & evidence

ORD record
ord-a89d0faebb254d5ca2b2c01ce744358e
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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