Hydrochloric Acid → 3-(6-Bromo-3-pyridinyl)-2-propenal

HRID 992934Notes

Reaction equation

HRID 992934 reaction equation
CC([Mg]Cl)C.[Br:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][N:8]=1.CN(C)[CH:16]=[CH:17][CH:18]=[O:19].Cl>C1COCC1>[Br:6][C:7]1[N:8]=[CH:9][C:10]([CH:16]=[CH:17][CH:18]=[O:19])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 693532,5-DibromopyridineHCID 791253-(Dimethylamino)-2-propenalHCID 178418918HCID 178418918, compound

Product 1

HCID 739903903-(6-Bromo-3-pyridinyl)-2-propenalYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Propylmagnesium chloride (2.0 M in THF, 5.00 mL 10.00 mmol) was added to a solution of 2,5-dibromopyridine (2.37 g, 10.00 mmol) in THF (5.0 mL) at RT. The resulting brown suspension was stirred for 1 h and then cooled to 0° C. 3-Dimethylaminoacrolein (95%, 1.30 mL, 12.36 mmol) was added and the mixture was warmed to RT and stirred for 2 h. 2 N HCl was added and after 5 min the mixture was cooled to 0° C. The precipitated solids were removed by filtration and partitioned between ethyl acetate (75 mL) and 10% NaOH (25 mL). The ethyl acetate layer was washed with brine (25 mL), dried (MgSO4), and concentrated. Recrystallization from ethyl acetate provided 550 mg (26%) of the title compound as shiny brown flakes. MS 211 (M+H)+.

Workup

  1. temperaturethe mixture was warmed to RT
  2. stirringstirred for 2 h
  3. temperaturewas cooled to 0° C
  4. customThe precipitated solids were removed by filtration
  5. custompartitioned between ethyl acetate (75 mL) and 10% NaOH (25 mL)
  6. washThe ethyl acetate layer was washed with brine (25 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2ae18c9e397e4663a74715cd69d6cb87
Source dataset
uspto-grants-2002_10
Patent number
US06472372B1

Reaction notes

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