Triethylamine → HCID 86592825, compound

HRID 857160Notes

Reaction equation

HRID 857160 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[C:11]([Br:13])[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17](I)[CH:16]=2)=[C:9]([Br:23])[CH:8]=1)(C)[C:3]([O-:5])=[O:4].[C:24]1([CH3:32])[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[CH:31])[CH:25]=1.[CH2:33](N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.ClCCl>[Br:23][C:9]1[CH:8]=[C:7]([CH:2]([CH3:1])[C:3]([O:5][CH3:33])=[O:4])[CH:12]=[C:11]([Br:13])[C:10]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]2[O:21][C:30]([C:26]3[CH:25]=[C:24]([CH3:32])[CH:29]=[CH:28][CH:27]=3)=[CH:31][C:17]=2[CH:16]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1366003-MethylphenylacetyleneHCID 86592826HCID 86592826, compound

Product 1

HCID 86592825HCID 86592825, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl[3,5-dibromo-4-(4-hydroxy-3-iodophenoxy)phenyl]propionate (17 mg), 3-tolylacetylene (20 mg) and bis(triphenylphosphine)palladium(II) chloride (2.0 mg), copper(I) iodide (1.0 mg) and triethylamine (1 mL) was stirred at reflux. After 2 hours, the reaction mixture was cooled down, dichloromethane was added and washed once with a saturated solution of aqueous ammonium chloride. The organic phase concentrated and the residue purified on column (silica gel, n-heptane/ethyl acetate 8:2), to give 19 mg of methyl {3,5-dibromo-4-[2-(3-tolyl)-5-benzofuranyloxy]phenyl}propionate as a pale yellow solid mass. 1H-NMR (270 MHz, Acetone-d6): δ 7.68 (s, 2H), 7.53 (dd, 1H), 7.36 (t, 2H), 7.21 (d, 2H), 6.89 (m, 2H), 3.64 (s, 3H), 2.98 (t, 2H), 2.74 (t, 2H), 2.40 (s, 3H).

Workup

  1. temperatureat reflux
  2. temperaturethe reaction mixture was cooled down
  3. washwashed once with a saturated solution of aqueous ammonium chloride
  4. concentrationThe organic phase concentrated
  5. customthe residue purified on column (silica gel, n-heptane/ethyl acetate 8:2)

Sources & evidence

ORD record
ord-093a1d9cf1954763852e1fb517a920cf
Source dataset
uspto-grants-2006_12
Patent number
US07144909B2

Reaction notes

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