Triethylamine → 3-[(4-Fluorophenyl)ethynyl]aniline

HRID 1030865

Reaction equation

HRID 1030865 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:16][C:17]1[CH:18]=[C:19]([C:23]#[CH:24])[CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1.[Pd].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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:24]#[C:23][C:19]2[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=2)[NH2:16])=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 99931-Bromo-4-fluorobenzeneHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 198838813-[(4-Fluorophenyl)ethynyl]anilineYield 96.4%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 10122028Bis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

A multinecked flask as described in Example 1 was charged with 50.0 g (0.28 mol) of p-bromofluorobenzene, 200 ml of dried, degassed triethylamine, 35.0 g (0.30 mol) of 3-aminophenylacetylene, 0.23 g (0.29 mmol) of bis(triphenyl phosphine) palladium II chloride, 1.03 g (3.92 mmol) of triphenylphosphine, and 0.1 g (0.52 mmol) of cuprous iodide. The reaction mixture was heated at 65° C. for 48 hours at which point gas chromatography showed the reaction to be complete. The mixture was cooled to room temperature and diluted with 200 ml of toluene. The toluene/triethylamine solution was decanted and concentrated on the rotary evaporator to give 75 g (0.27 mol, 96% yield) of the product as a bright yellow solid.

Workup

  1. customA multinecked flask as described in Example 1
  2. customof dried
  3. customthe reaction
  4. temperatureThe mixture was cooled to room temperature
  5. customThe toluene/triethylamine solution was decanted
  6. concentrationconcentrated on the rotary evaporator

Sources & evidence

ORD record
ord-f533ca28edf546b5a71de855a664c98e
Source dataset
uspto-grants-1992_04
Patent number
US05107026

Linked notes

Loading…