Toluene → HCID 22922829, compound

HRID 2257433Notes

Reaction equation

HRID 2257433 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21](Br)=[C:20]([F:25])[CH:19]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[CH:39](/B(O)O)=[CH:40]\[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21](/[CH:39]=[CH:40]/[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[C:20]([F:25])[CH:19]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 5942337trans-Nonenylboronic acidHCID 22922867HCID 22922867, compound

Product 1

HCID 22922829HCID 22922829, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

In a four necked flask equipped with a thermometer and a stirrer, 1-(4-octyloxylphenyl)-2-(4-bromo-3-fluorophenyl)acetylene (4.8 g, 0.012 mol), tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol), toluene (50 ml), sodium carbonate (10.6 g, 0.1 mol) and water (90 ml) were charged. Then, to the mixture, E-1-nonenyl-dihydroxyborane (2.5 g, 0.015 mol) was added and reacted at a temperature of 80° to 85° C. for 6 hours. After cooling the reaction mixture, the aqueous layer was separated off, and the organic layer was washed with water. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1-(4-octyloxyphenyl)-2-[4-(1-trans-nonenyl)-3-fluorophenyl]acetylene (3.9 g). Yield: 73%.

Workup

  1. additionwere charged
  2. customreacted at a temperature of 80° to 85° C. for 6 hours
  3. temperatureAfter cooling the reaction mixture
  4. customthe aqueous layer was separated off
  5. washthe organic layer was washed with water
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8d119153d9e248819d3d27a894433640
Source dataset
uspto-grants-1997_08
Patent number
US05658489

Reaction notes

Loading…