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

HRID 413939Notes

Reaction equation

HRID 413939 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>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[CH:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 138235471,3-Dichloro-5-ethynylbenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3,5-dichloro-phenylethynyl)-trimethylsilane (4.85 g, 19.9 mmol) in methanol (50 mL) was added 1M potassium hydroxide (30 mL). The reaction mixture was stirred 1 h at room temperature and evaporated. The residue was treated with water (10 mL) and extracted with 3×40 mL diethyl ether. The tried organic phases were evaporated to give the desired 1,3-dichloro-5-ethynyl-benzene product in 2.3 g yield.

Workup

  1. customevaporated
  2. additionThe residue was treated with water (10 mL)
  3. extractionextracted with 3×40 mL diethyl ether
  4. customThe tried organic phases were evaporated

Sources & evidence

ORD record
ord-af94009c5e254f698fc70f31fcd57cb7
Source dataset
uspto-grants-2003_05
Patent number
US06569901B2

Reaction notes

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