Potassium Hydroxide → 1,3-Dichloro-5-ethynylbenzene

HRID 24011Notes

Reaction equation

HRID 24011 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][Si](C)(C)C)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[K+]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[CH:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22570337[2-(3,5-Dichlorophenyl)ethynyl]trimethylsilane

Product 1

HCID 138235471,3-Dichloro-5-ethynylbenzeneYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of (3,5-dichloro-phenylethynyl)-trimethyl-silane (1.97 g, 8.1 mmol) in methanol (40 mL) was added a solution of potassium hydroxide (6.8 mg, 0.12 mmol) in H2O (0.24 mL). After stirring at ambient temperature for 40 minutes, the reaction mixture was diluted with water (40 mL), and extracted with hexane until the extracting solvent showing no product by TLC. The combined organic layer was dried over MgSO4, and concentrated to give the title compound (1.21 g, 87% yield) as a white solid. 1H NMR (CDCl3) δ 7.37-7.34 (m, 3H), 3.15 (s, 1H).

Workup

  1. extractionextracted with hexane until the extracting solvent
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-330c0c3ee0b143eea7324012c8728a63
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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