4-Acetyl-2-methoxyphenyl trifluoromethanesulfonate → HCID 21956529, compound

HRID 2213090Notes

Reaction equation

HRID 2213090 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][C:8]=1[O:16][CH3:17])(=O)=O.[Br-].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Zn+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][O:16][C:8]1[CH:9]=[C:10]([C:13](=[O:15])[CH3:14])[CH:11]=[CH:12][C:7]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=1

Participants

5

Reactant 2

HCID 121936284-Acetyl-2-methoxyphenyl trifluoromethanesulfonateHCID 178418723HCID 178418723, compound

Product 1

HCID 21956529HCID 21956529, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-acetyl-2-methoxyphenyl trifluoromethanesulfonate (5.8 g, 19.5 mmol) in THF (100 mL) was degassed by bubbling argon through the solution for 15 min, then treated with 2-pyridylzinc bromide (39 mL of 0.5M in THF, 19.5 mmol) and Pd(PPh3)4 (1.1 g, 0.97 mmol). The resulting reaction mixture was degassed again and heated to reflux for 12 h under an atmosphere of argon. The reaction mixture was cooled to rt, concentrated and purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 2:3) to afford 1-(3-methoxy-4-pyridin-2-ylphenyl)ethanone.

Workup

  1. customby bubbling argon through the solution for 15 min
  2. customThe resulting reaction mixture
  3. customwas degassed again
  4. temperatureheated
  5. temperatureto reflux for 12 h under an atmosphere of argon
  6. concentrationconcentrated
  7. custompurified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 2:3)

Sources & evidence

ORD record
ord-d737fbf3243e43c78e10f21130a6b8f9
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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