Tributylamine → HCID 22321883, compound

HRID 496642Notes

Reaction equation

HRID 496642 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[CH2:21])=[CH:18][CH:17]=1.C(N(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>ClCCl.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O>[F:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[C:21][C:2]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 7622TributylamineHCID 678834-FluorostyreneHCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 516892Sodium Bicarbonate

Product 1

HCID 22321883HCID 22321883, compound

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 2-bromo-5-nitrobenzoate (5 g), 4-fluorostyrene (3.5 g), tributylamine (0.39 g), bis-(triphenylphosphine)-palladium(II)chloride (0.3 g), sodium bicarbonate (2.65 g) and water (30 ml) was stirred and heated at reflux under an argon atmosphere for 1.5 hours. The reaction was then cooled, suspended in dichloromethane (200 ml) and passed through a pad of silica (chromatography grade) eluting with more dichloromethane The dichloromethane was then evaporated away and the residue treated with iso-hexane (200 ml) to give methyl 2-[2-(4-fluorophenyl)ethynyl]-5-nitrobenzoate (compound 74) as a yellow precipitate which was filtered and dried, (5.05 g).

Workup

  1. temperatureheated
  2. temperatureat reflux under an argon atmosphere for 1.5 hours
  3. temperatureThe reaction was then cooled
  4. washeluting with more dichloromethane The dichloromethane
  5. customwas then evaporated away
  6. additionthe residue treated with iso-hexane (200 ml)

Sources & evidence

ORD record
ord-a613a5e0c3af4116812696498bbd08b5
Source dataset
uspto-grants-2005_09
Patent number
US06946468B1

Reaction notes

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