Hydrochloric Acid → HCID 89654505, compound

HRID 2275389Notes

Reaction equation

HRID 2275389 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:20])[C:8](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1OS(C(F)(F)F)(=O)=O.[CH2:29]([C:33]1[CH:37]=[CH:36][S:35][C:34]=1[C:38]#[CH:39])[CH2:30][CH2:31][CH3:32].O.Cl>C(N(CC)CC)C.C1COCC1.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>[CH2:29]([C:33]1[CH:37]=[CH:36][S:35][C:34]=1[C:38]#[C:39][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:39]#[C:38][C:34]3[S:35][CH:36]=[CH:37][C:33]=3[CH2:29][CH2:30][CH2:31][CH3:32])[C:7]=2[Cl:20])[C:2]=1[Cl:1])[CH2:30][CH2:31][CH3:32]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 15442609HCID 15442609, compoundHCID 45112268HCID 45112268, compound

Product 1

HCID 89654505HCID 89654505, compoundYield 33%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

1.46 g (2.96 mmol) of [1,5-dichloro-6-(trifluoromethylsulfonyloxy)-2-naphthyl]trifluoro-methanesulfonate (17) and 1.46 g (8.89 mmol) of 3-butyl-2-ethynylthiophene (18) are dissolved in 1.25 ml of dry triethylamine and 30 ml of dry THF. To the reaction mixture are added 208 mg (0.30 mmol) of Pd(PPh3)2Cl2 and 113 mg (0.59 mmol) of copper(I) iodide. The mixture is heated under reflux for 20 h. 3 ml of water and 3 ml of 1N HCl solution are added thereto, the phases are separated and the aqueous phase is extracted three times with 25 ml of DCM. The combined organic phases are dried over sodium sulfate. After the solvents have been distilled off, the residue is recrystallized from hexane/chloroform to obtain 505 mg (33%) of product. 1H NMR (CDCl3): 8.22 ppm (d, 2H), 7.68 (d, 2H), 7.27 (d, 2H), 6.94 (d, 2H), 2.88 (dd, 4H), 1.70 (m, 4H), 1.42 (qa, 4H), 0.96 (t, 6H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 20 h
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted three times with 25 ml of DCM
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. distillationAfter the solvents have been distilled off
  7. customthe residue is recrystallized from hexane/chloroform

Sources & evidence

ORD record
ord-b4eb9c96e1fd4cac98b1428f648bffa7
Source dataset
uspto-grants-2015_09
Patent number
US09127020B2

Reaction notes

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