Hydrochloric Acid → 3,4-Difluorophenylacetylene

HRID 606795Notes

Reaction equation

HRID 606795 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([C:15]#[C:16][Si](C)(C)C)[CH:11]=[CH:12][C:13]=1[F:14].Cl>C(O)C>[C:15]([C:10]1[CH:11]=[CH:12][C:13]([F:14])=[C:8]([F:7])[CH:9]=1)#[CH:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67047877((3,4-Difluorophenyl)ethynyl)trimethylsilane

Product 1

HCID 138784543,4-DifluorophenylacetyleneYield 76.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add potassium carbonate (719 mg, 5.2 mmol) to a solution of (3,4-difluorophenylethynyl)-trimethylsilane (2.20 g, 10.4 mmol) in ethanol (30 mL). Stir at room temperature for 16 h. Neutralize with 10% aqueous hydrochloric acid. Add water and extract the product with hexanes. Concentrate hexanes slowly in a cooled water bath (˜10° C.) to give the title compound (1.10 g, 76%).

Workup

  1. extractionAdd water and extract the product with hexanes

Sources & evidence

ORD record
ord-a78c066ac43c4c46b06d6c12f202b448
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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