1,1,1-Trichloroethane → HCID 18420200, compound

HRID 990250Notes

Reaction equation

HRID 990250 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].[Br:9]N1C(=O)CCC1=O.[Cl:17]C(Cl)(Cl)C>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[ClH:17].[Br:9][CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 62781,1,1-TrichloroethaneHCID 75232-EthylpyridineHCID 67184N-bromobutanimide

Product 1

HCID 18420200HCID 18420200, compound

Reagents, catalysts & solvents 1

HCID 7187Benzoyl PeroxideCatalyst

Procedure

A mixture of 2-ethylpyridine (20.0 g, 187 mmol), N-bromosuccinimide (38.0 g, 213 mmol), and benzoyl peroxide (1.0 g, 75% in water) in 1,1,1-trichloroethane (200 ml), was heated under reflux for 3 hours. The cooled mixture was filtered, and the filtrate washed with water (2×100 ml), aqueous sodium thiosulphate solution (100 ml), and brine (100 ml). The solution was dried (MgSO4), filtered through charcoal, and then hydrobromic acid (25 ml, 62%) added. This solution was concentrated under reduced pressure and azeotroped with toluene to give 2-(1-bromoethyl)pyridine hydrochloride as a dark oil (66.0 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe cooled mixture was filtered
  4. washthe filtrate washed with water (2×100 ml), aqueous sodium thiosulphate solution (100 ml), and brine (100 ml)
  5. dry with materialThe solution was dried (MgSO4)
  6. filtrationfiltered through charcoal
  7. additionhydrobromic acid (25 ml, 62%) added
  8. concentrationThis solution was concentrated under reduced pressure
  9. customazeotroped with toluene

Sources & evidence

ORD record
ord-684c9438545843618459aa17a5aa1540
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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