Potassium Hydroxide → 1-Bromo-4-(2-(4-hexylphenyl)ethynyl)benzene

HRID 1454428Notes

Reaction equation

HRID 1454428 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][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[OH-].[K+]>O1CCOCC1.CO.O>[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][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 57530613HCID 57530613, compound

Product 1

HCID 575306161-Bromo-4-(2-(4-hexylphenyl)ethynyl)benzeneYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 2 L flask containing a solution of 1-bromo4-[(Z)-2-chloro-2-(4-hexylphenyl) vinyl] benzene (VIb) (209.79 g; 555.37 mmol) in 1,4-dioxane (1000 mL; 4.8 vols) and MeOH (300 mL; 1.4 vols), KOH (62.32 g; 1110.73 mnmol) was added in one portion. Reaction mixture was stirred at 80° C. overnight. Volume was reduced under vacuum to 200 mL and the residue was taken up in water (2000 mL). The resulting suspension was filtered and washed with water to give a clear beige solid. Drying under vacuum at 33° C. overnight gave the title compound (m=173.34 g) in a 92% yield. Melting point: 67° C. 1H-NMR (CDlC3=7.26 ppm): 7.47 (d, J=8.66 Hz, 2H), 7.43 (d, J=8.10 Hz, 2H), 7.37 (d, J=8.28 Hz, 2H), 7.16 (d, J=8.10 Hz, 2H), 2.61 (t, J=7.81 Hz, 2H), 1.59 (quint, J=7.48 Hz, 2H), 1.42-1.21 (br s, 6H), 0.88 (t, J=6.31 Hz, 3H)

Workup

  1. additionwas added in one portion
  2. customReaction mixture
  3. filtrationThe resulting suspension was filtered
  4. washwashed with water
  5. customto give a clear beige solid
  6. customDrying under vacuum at 33° C. overnight

Sources & evidence

ORD record
ord-0f74e81ce03e4c0484973ef612e19961
Source dataset
uspto-grants-2009_01
Patent number
US07479575B2

Reaction notes

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