4-Bromo-1,2-difluorobenzene → HCID 63997889, compound

HRID 1974771Notes

Reaction equation

HRID 1974771 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][C:7]=1[F:8].[NH2:10][C:11]([CH3:15])([CH3:14])[C:12]#[CH:13]>[Pd+2].[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>[NH2:10][C:11]([CH3:15])([CH3:14])[C:12]#[C:13][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1

Participants

7

Reactant 2

HCID 676754-Bromo-1,2-difluorobenzeneHCID 763193-Butyn-2-amine, 2-methyl-

Product 1

HCID 63997889HCID 63997889, compoundYield 87.7%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 84124Bis(triphenylphosphine)palladium chlorideCatalystHCID 8471TriethylamineSolvent

Procedure

155 g (0.8 mol) of 3,4-difluoro-bromobenzene and 75 g (0.9 mol) of 3-amino-3, 3-dimethyl-1-propine are introduced into 900 ml of triethylamine. After 2.81 g (0.004 mol) of palladium(II)-bis(triphenylphosphine) dichloride, 3.05 g (0.016 mol) of copper(I) iodide and 8.4 g (0.032 mol) of triphenylphosphine have been added, the reaction mixture is refluxed for 4 hours. It is subsequently filtered, the filtrate is concentrated under a water-pump vacuum, and the residue is distilled under an oil-pump vacuum. 137 g (86% of theory) of 3-amino-3,3-dimethyl-1-(3,4-difluoro-phenyl)-1-propine of boiling point 75° C. at 1.5 mbar are obtained.

Workup

  1. temperaturethe reaction mixture is refluxed for 4 hours
  2. filtrationIt is subsequently filtered
  3. concentrationthe filtrate is concentrated under a water-pump vacuum
  4. distillationthe residue is distilled under an oil-pump vacuum

Sources & evidence

ORD record
ord-7fba9f90dd674fddbf31fb14e15379d0
Source dataset
uspto-grants-1994_02
Patent number
US05283363

Reaction notes

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