Triethylamine → HCID 14088833, compound

HRID 2207322Notes

Reaction equation

HRID 2207322 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1I.C(N(CC)CC)C.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[CH:27])=[CH:22][CH:21]=1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:27]#[C:26][C:23]1[CH:24]=[CH:25][C:20]([Br:19])=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 136603Benzene, 1-bromo-4-ethynyl-

Product 1

HCID 14088833HCID 14088833, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-iodo-benzoic acid methyl ester (1.31 g, 5.00 mmol) in DMF (10 ml) are added bis(triphenylphosphine)-palladium(II)-chloride (351 mg, 0.50 mmol), copper(I) iodide (28.5 mg, 0.15 mmol), triethylamine (2.08 ml, 15.0 mmol) and 1-bromo-4-ethynyl-benzene (905 mg, 5.00 mmol). The resulting dark brown solution is flushed with nitrogen, heated to 80° C. and stirred in a closed reaction vial at this temperature for 16 hours. The reaction mixture is allowed to cool to room temperature and partitioned between water and dichloromethane. The organic phase is washed with 1 N HCl, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 2-(4-bromo-phenylethynyl)-benzoic acid methyl ester as brown oil; HPLC/MS 3.46 min (B), [M+H] 315/317.

Workup

  1. customThe resulting dark brown solution is flushed with nitrogen
  2. temperatureto cool to room temperature
  3. custompartitioned between water and dichloromethane
  4. washThe organic phase is washed with 1 N HCl
  5. dry with materialdried over sodium sulfate
  6. customevaporated under vacuum
  7. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-71ec6d75f1c2421c9a10f84bb7761851
Source dataset
uspto-grants-2016_06
Patent number
US09376433B2

Reaction notes

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