Hydrochloric Acid → (5-Bromo-pyrimidine-2-yl)-phenyl-methanone

HRID 2381956Notes

Reaction equation

HRID 2381956 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]#N)=[N:6][CH:7]=1.CC[O:12]CC.[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>O.C1COCC1>[Br:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6865465-Bromopyrimidine-2-carbonitrileHCID 178418255HCID 178418255, compound

Product 1

HCID 67360359(5-Bromo-pyrimidine-2-yl)-phenyl-methanoneYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-pyrimidine-2-carbonitrile (2.5 g, 13.59 mmol) is dissolved ether (30 mL), and PhMgBr (3 ether solution, 13.59 mmol, 4.53 mL) is added dropwise at rt. The mixture is heated to reflux for 3 h under N2, and then cooled to rt. THF (30 mL) is added followed by the addition of 2 N aqueous HCl (10 mL). The resulting solution is stirred at rt for 30 min, and water (30 mL) is added. The aqueous layer is extracted with EtOAc (3×20 mL). The combined organic layer is washed with saturated aqueous NaHCO3 (15 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting 70% EtOAc in heptane to afford (5-bromo-pyrimidine-2-yl)-phenyl-methanone (3.01 g, 84%) as a solid. MS: 264 (M+H).

Workup

  1. additionis added dropwise at rt
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 3 h under N2
  4. extractionThe aqueous layer is extracted with EtOAc (3×20 mL)
  5. washThe combined organic layer is washed with saturated aqueous NaHCO3 (15 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by silica gel chromatography
  10. washeluting 70% EtOAc in heptane

Sources & evidence

ORD record
ord-78a3eace758042b9815941ff109486be
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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