Potassium Carbonate → HCID 86762364, compound

HRID 2367906Notes

Reaction equation

HRID 2367906 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)(C)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CO>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)=[CH:9][CH:8]=1)#[CH:5]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 11843651((4-((4-Fluorophenyl)ethynyl)phenyl)ethynyl)trimethylsilane

Product 1

HCID 86762364HCID 86762364, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-(trimethylsilylethynyl)-4-(4-fluorophenylethynyl)benzene (2.2 g, 7.5 mmol) was dissolved in CH2Cl2 (30 mL) diluted with MeOH (30 mL) and then treated with powdered K2CO3 (2.1 g, 15 mmol) and allowed to stir at ambient temperature for 20 h under N2. The reaction mixture was filtered to remove solids, concentrated, redissolved in CH2Cl2, washed with water (2×), brine, dried over MgSO4, filtered and concentrated to dryness to give 1.43 g (87%) product that was used as is in the next reaction. 1H NMR, (CDCl3) δ: 7.54 (m, 2H), 7.49 (m, 4H); 7.05 (t, J=8.4 Hz, 2H); 3.20 (s, 1H). 13C {1H} NMR (CDCl3): 162.6 (J=250.3 Hz), 133.6 (J=8.0 Hz), 132.1, 131.4, 123.6, 122.0, 119.1 (J=3.6 Hz), 115.7 (J=32.0 Hz), 90.3, 88.6, 83.3, 79.0 ppm.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove solids
  3. concentrationconcentrated
  4. dissolutionredissolved in CH2Cl2
  5. washwashed with water (2×), brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8826b5a7f1c246bdac9bf9208cdbb237
Source dataset
uspto-grants-2014_04
Patent number
US08703388B2

Reaction notes

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