Propargyl bromide → 4-Fluoro-N-(prop-2-yn-1-yl)aniline

HRID 1722705Notes

Reaction equation

HRID 1722705 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]#[CH:12].C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:12][C:11]#[CH:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 97314-FluoroanilineHCID 81531Diisopropylethylamine

Product 1

HCID 146500364-Fluoro-N-(prop-2-yn-1-yl)aniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 9.47 ml (0.1 mol) of 4-fluorobenzenamine, 16.36 g (0.11 mol) of an 80% solution of 3-bromo-1-propyne in toluene, and 17.43 ml (0.11 mol) of N-ethyl-N-(1-methylethyl)-2-propanamine in 350 ml of toluene is heated at 90° C. for three hours. Ethyl acetate is added to the reaction suspension, and it is washed three times with water. The organic layer is separated, dried (magnesium sulfate), and concentrated to give 15.5 g of a dark brown liquid. This is applied to a column of 1 kg of flash silica gel packed in heptane-dichloromethane (5:1). Elution with the same solvent gives 9.09 g (61%) of the product as a yellow oil.

Workup

  1. washis washed three times with water
  2. customThe organic layer is separated
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f767ab45708a4eb6b03112c05d2a8208
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

Loading…