Potassium Carbonate → HCID 67111585, compound

HRID 540777Notes

Reaction equation

HRID 540777 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[C:2]#[CH:3].[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](I)[CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[Br:8][C:9]1[CH:10]=[C:11]([C:3]#[C:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 12182Ethyl propiolate

Product 1

HCID 67111585HCID 67111585, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

Ethyl propiolate (2.15 mL, 21.2 mmol, 1.20 equiv) was added to a mixture of 1-bromo-3-iodobenzene (5.00 g, 17.7 mmol, 1 equiv), PdCl2(CH3CN)2 (367 mg, 1.41 mmol, 0.080 equiv), copper (1) iodide (135 mg, 0.707 mmol, 0.040 equiv) and potassium carbonate (2.93 g, 21.2 mmol, 1.20 equiv) in N,N-dimethylformamide (44 mL) at 22° C. The reaction mixture was stirred for 1 hour, then was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic layer was washed sequentially with water and saturated aqueous sodium chloride solution. The washed solution was dried over sodium sulfate, and the dried solution was filtered. The filtrate was concentrated, and the residue was purified by flash-column chromatography on silica gel (hexanes, grading to 40% ethyl acetate-hexanes) to afford ethyl 3-(3-bromophenyl)prop-2-ynoate (1.08 g, 24%). Calc'd (M+1)+: 253.0. Found: 252.9.

Workup

  1. customwas partitioned between ethyl acetate and saturated aqueous ammonium chloride solution
  2. washThe organic layer was washed sequentially with water and saturated aqueous sodium chloride solution
  3. dry with materialThe washed solution was dried over sodium sulfate
  4. filtrationthe dried solution was filtered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash-column chromatography on silica gel (hexanes, grading to 40% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-229830071c9e4911aa4709ac956582eb
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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