Hydrochloric Acid → 1-(4-Bromo-2-chlorophenyl)methanamine--hydrogen chloride (1/1)

HRID 251856Notes

Reaction equation

HRID 251856 reaction equation
[Br:1][C:2]1([Cl:10])[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH2:3]1.[ClH:11].[OH-].[Na+]>C1COCC1>[ClH:10].[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([Cl:11])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66861105HCID 66861105, compound

Product 1

HCID 534078891-(4-Bromo-2-chlorophenyl)methanamine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

46.2 ml of borane-THF complex are provided under ice cooling. A solution of 2.0 g of 4-bromo-4-chlorobenzonitrile in 240 ml of THF is added slowly. The reaction mixture is then heated for 1 h under reflux, cooled and 20 ml of 1N hydrochloric acid are added dropwise while cooling on ice. The mixture is heated under reflux for 1 h and left to cool. For the work-up the solution is adjusted to an alkaline pH with a 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated on a rotary evaporator. 6 ml of hydrochloric acid in dioxane (4N) are added and the precipitated hydrochloride is collected by suction filtration. 1.3 g of product are obtained.

Workup

  1. custom46.2 ml of borane-THF complex are provided under ice cooling
  2. temperatureThe reaction mixture is then heated for 1 h
  3. temperatureunder reflux
  4. temperaturecooled
  5. temperaturewhile cooling on ice
  6. temperatureThe mixture is heated
  7. temperatureunder reflux for 1 h
  8. waitleft
  9. temperatureto cool
  10. extractionextracted with dichloromethane
  11. dry with materialThe organic phase is dried over sodium sulfate
  12. concentrationconcentrated on a rotary evaporator
  13. addition6 ml of hydrochloric acid in dioxane (4N) are added
  14. filtrationthe precipitated hydrochloride is collected by suction filtration

Sources & evidence

ORD record
ord-cf5f292d95eb42e29d63e43667c39795
Source dataset
uspto-grants-2011_01
Patent number
US07867992B2

Reaction notes

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