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

HRID 1454432Notes

Reaction equation

HRID 1454432 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]([CH2:16][CH3:17])=[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]([CH2:16][CH3:17])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 156063231-bromo-4-[(Z)-2-chloro-2-(4-ethylphenyl) vinyl] benzene

Product 1

HCID 575306181-Bromo-4-[(4-ethylphenyl)ethynyl]benzeneYield 99.2%

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-ethylphenyl) vinyl] benzene (VIc) (9.540 g; 29.66 mmol) in 1,4-dioxane (48 mL; 5 vols) and MeOH (14 mL; 1.5 vols), KOH (3.328 g; 59.32 mmol) was added in one portion. Protocol and work-up was then similar with those described above. Title compound (m=8.39 g) was obtained in a 99% yield. Melting point: 117° C.

Workup

  1. additionwas added in one portion

Sources & evidence

ORD record
ord-32fd1a821da04538be4072213bd32eab
Source dataset
uspto-grants-2009_01
Patent number
US07479575B2

Reaction notes

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