2-Bromopyridine → Ethyl 4-(pyridin-2-yl)benzoate

HRID 2185016Notes

Reaction equation

HRID 2185016 reaction equation
[I-].[CH2:2]([O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([Zn+])=[CH:9][CH:8]=1)=[O:6])[CH3:3].Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>O1CCCC1.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>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:10]1[CH:11]=[CH:12][C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 79732-BromopyridineHCID 178469116HCID 178469116, compound

Product 1

HCID 14097203Ethyl 4-(pyridin-2-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

4-(Ethoxycarbonyl)phenylzinc iodide in tetrahydrofuran (0.5M, 2 mL, 1 mmol) was added to a solution of 2-bromopyridine (0.16 g, 1 mmol) and tetrakis(triphenylphosphine)palladium(0) (63 mg, 0.05 mmol) in tetrahydrofuran (5 mL) and stirred at RT for 3 h. The reaction was quenched with saturated ammonium chloride and extracted three times with ethyl acetate. The combined organic phase was dried (MgSO4), concentrated in vacuo, and the residue chromatographed (silica gel, 10% ethyl acetate/hexane) to give the title compound as a yellow solid (0.15 g).

Workup

  1. customThe reaction was quenched with saturated ammonium chloride
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe residue chromatographed (silica gel, 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a8f7b4ad236e48878902694eebe93e71
Source dataset
uspto-grants-2002_06
Patent number
US06399656B1

Reaction notes

Loading…