Potassium Carbonate → 1-Chloro-3-ethynylbenzene

HRID 606791Notes

Reaction equation

HRID 606791 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9]C(C)(O)C)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[CH:9])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 230063744-(3-Chlorophenyl)-2-methyl-3-butyn-2-ol

Product 1

HCID 1230861-Chloro-3-ethynylbenzeneYield 66.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Add dry toluene to a degassed mixture of 4-(3-chlorophenyl)-2-methylbut-3-yn-2-ol (21.1 g, 0.109 mol), potassium carbonate (45 g, 0.326 mol) and 18-crown-6 (6.89 g, 0.026 mol). Stir at 90° C. for 36 h. Cool the reaction mixture to room temperature, filter and wash with toluene. Concentrate and purify the residue by silica gel chromatography, eluting with 18:1 o 13:1 hexanes:ethyl acetate, to give the title compound (9.85 g, 66%).

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. filtrationfilter
  3. washwash with toluene
  4. concentrationConcentrate
  5. custompurify the residue by silica gel chromatography
  6. washeluting with 18:1 o 13:1 hexanes

Sources & evidence

ORD record
ord-b46969bcf8b0465daccdc5e39da688a3
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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