Bromoethene → 1-(4-Chlorophenyl)-1-(3-pyridyl)-2-propen-1-ol

HRID 1649541Notes

Reaction equation

HRID 1649541 reaction equation
[CH:1](Br)=[CH2:2].[Mg].[Cl:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:8][CH:7]=1.[Cl-].[NH4+]>O1CCCC1.O>[Cl:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)([OH:11])[CH:1]=[CH2:2])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 11641BromoetheneHCID 25517Ammonium ChlorideHCID 845184-Chlorophenyl pyridin-3-yl ketoneHCID 5462224Magnesium

Product 1

HCID 127170981-(4-Chlorophenyl)-1-(3-pyridyl)-2-propen-1-olYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of vinylbromide (38.4 g, 359 mmol) in 100 ml tetrahydrofuran was added to a mixture of magnesium (9.15 g, 377 mmol) in 40 ml tetrahydrofuran under a nitrogen atmosphere at 50° to 60° C. After reflux for 1 h 3-(4-chlorobenzoyl)pyridine (62.4 g, 287 mmol) in 250 ml tetrahydrofuran was added at 10° C. After stirring for 1 h a solution of 20 g ammonium chloride in 100 ml water was added and the mixture filtered. The organic phase was evaporated and the residue taken up in ether and treated with charcoal. After filtration the solvent was evaporated to give 62.6 g (89%) of a brownish oil which solidified. Recrystallisation from toluene gave a product having m.p. 82.5°-84° C.

Workup

  1. additionwas added at 10° C
  2. additionwas added
  3. filtrationthe mixture filtered
  4. customThe organic phase was evaporated
  5. additiontreated with charcoal
  6. filtrationAfter filtration the solvent
  7. customwas evaporated

Sources & evidence

ORD record
ord-bd2802f54f0648ae968021439f8855d2
Source dataset
uspto-grants-1983_11
Patent number
US04418065

Reaction notes

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