N-bromobutanimide → 2-Bromomethyl-4-tert-butyl-6-chloro-pyridine

HRID 1446720Notes

Reaction equation

HRID 1446720 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([CH3:12])[N:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:13][CH2:12][C:4]1[CH:5]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:7]=[C:2]([Cl:1])[N:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 601265994-Tert-butyl-2-chloro-6-methylpyridine

Product 1

HCID 866343052-Bromomethyl-4-tert-butyl-6-chloro-pyridineYield 44.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Dissolve 2-chloro-6-methyl-4-tert-butyl-pyridine (3.00 g, 16.33 mmol), N-bromosuccinimide (3.20 g, 17.97 mmol) and AIBN (0.03 g, 0.16 mmol) in carbon tetrachloride (60 mL) and heat to reflux. After heating for 6 hours, stir the contents overnight at ambient temperature. The contents are then concentrated to dryness and dry loaded onto a silica plug and eluted with dichloromethane to obtain the title compound (1.90 g, 7.23 mmol). MS(ES), m/z 263 (M+1).

Workup

  1. temperatureheat to reflux
  2. temperatureAfter heating for 6 hours
  3. concentrationThe contents are then concentrated to dryness
  4. customdry
  5. washeluted with dichloromethane

Sources & evidence

ORD record
ord-01f1f9d32d2449c4aa81d10a9882dbd7
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

Loading…