Hydrochloric Acid → (2-Bromo-4-chlorophenyl)methanamine

HRID 251855

Reaction equation

HRID 251855 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 234985242-Bromo-4-chlorobenzonitrile

Product 1

HCID 57794106(2-Bromo-4-chlorophenyl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13.9 ml of borane-THF complex are provided under ice cooling. A solution of 2.0 g of 2-bromo-4-chlorobenzonitrile (Example 65A) in 60 ml of THF is added slowly. The reaction mixture is then heated for 1 h under reflux, cooled and under ice cooling 20 ml of 1N hydrochloric acid are added dropwise. 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. The crude product is reacted further without purification.

Workup

  1. custom13.9 ml of borane-THF complex are provided under ice cooling
  2. temperatureThe reaction mixture is then heated for 1 h
  3. temperatureunder reflux
  4. additionare added dropwise
  5. temperatureThe mixture is heated
  6. temperatureunder reflux for 1 h
  7. waitleft
  8. temperatureto cool
  9. extractionextracted with dichloromethane
  10. dry with materialThe organic phase is dried over sodium sulfate
  11. concentrationconcentrated on a rotary evaporator
  12. customThe crude product is reacted further without purification

Sources & evidence

ORD record
ord-ad8e7abe5de8410fb6da2dc1a7bf6dda
Source dataset
uspto-grants-2011_01
Patent number
US07867992B2

Linked notes

Loading…