Propargyl bromide → Benzenamine, N-2-propyn-1-yl-4-(trifluoromethoxy)-

HRID 1722706Notes

Reaction equation

HRID 1722706 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.Br[CH2:14][C:15]#[CH:16].C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCCC.ClCCl>[CH2:16]([NH:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=1)[C:15]#[CH:14]

Participants

7

Reactant 4

HCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 14650037Benzenamine, N-2-propyn-1-yl-4-(trifluoromethoxy)-Yield 66.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 21907733Dichloromethane heptaneSolvent

Procedure

A solution of 8.86 g (50 mmol) of 4-(trifluoromethoxy)benzenamine, 8.18 g (55 mmol) of an 80% solution of 3-bromo-1-propyne in toluene, and 8.72 ml (50 mmol) of N-ethyl-N-(1-methylethyl)-2-propanamine in 200 ml of toluene is heated at 90° C. for eighteen hours. The suspension is cooled and treated with ethyl acetate. The suspension is washed several times with water. The ethyl acetate layer is separated, dried (magnesium sulfate), and concentrated to give a brown liquid. This is applied to a column of 1 kg of flash silica gel packed in n-heptane-dichloromethane (2:1). Elution with the same solvent gives 7.12 g (66.2%) of the product as a brown liquid.

Workup

  1. temperatureThe suspension is cooled
  2. washThe suspension is washed several times with water
  3. customThe ethyl acetate layer is separated
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customto give a brown liquid
  7. washElution with the same solvent

Sources & evidence

ORD record
ord-97384ccf920e42868cb46dba25b9d8f7
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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