Potassium Hydroxide → 1-Bromo-4-[(4-chlorophenyl)ethynyl]benzene

HRID 1454436Notes

Reaction equation

HRID 1454436 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\Cl)/[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[OH-].[K+]>O1CCOCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 575306171-bromo-4-[(Z)-2-chloro-2-(4-chlorophenyl) vinyl] benzene

Product 1

HCID 575306151-Bromo-4-[(4-chlorophenyl)ethynyl]benzeneYield 94.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a 100 mL flask containing a solution of 1-bromo-4-[(Z) -2-chloro-2-(4-chloro-phenyl) vinyl] benzene (VId) (7.89 g; 24.05 mmol) in 1,4-dioxane (40 mL; 5 vols) and MeOH (12 mL; 1.5 vols), KOH (2.699 g; 48.10 mmol) was added in one portion. Protocol and work-up was then similar with those described above. Title compound (m=6.598 g) was obtained in a 94% yield. Melting point: 179° C.

Workup

  1. additionwas added in one portion

Sources & evidence

ORD record
ord-4adc778f9ee24b0db4f02f069e467639
Source dataset
uspto-grants-2009_01
Patent number
US07479575B2

Reaction notes

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