1,3,5-Tribromobenzene → HCID 59323507, compound

HRID 2368798Notes

Reaction equation

HRID 2368798 reaction equation
Br[C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4](Br)[CH:3]=1.[CH2:10]([OH:15])[CH2:11][CH2:12][C:13]#[CH:14]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[OH:15][CH2:10][CH2:11][CH2:12][C:13]#[C:14][C:2]1[CH:7]=[C:6]([C:14]#[C:13][CH2:12][CH2:11][CH2:10][OH:15])[CH:5]=[C:4]([C:14]#[C:13][CH2:12][CH2:11][CH2:10][OH:15])[CH:3]=1

Participants

6

Reactant 2

HCID 122791,3,5-TribromobenzeneHCID 793464-Pentyn-1-ol

Product 1

HCID 59323507HCID 59323507, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

1,3,5-Tribromobenzene (10 g, 31.76 mmol), 4-pentyn-1-ol (10.69 g, 127.06 mmol) and bis(triphenylphosphine)palladium(II) dichloride were stirred in triethylamine under nitrogen for 5 minutes. Copper(I) iodide (92 mg, 0.48 mmol) was added and the mixture was stirred for 6 hours at 80° C. The mixture was cooled to room temperature, filtered through a celite pad and rinsed with ethyl acetate. The combined filtrate was evaporated to dryness under reduced pressure. The resulting residue was purified by column chromatography (CHCl3:MeOH 10:1) to afford 7.61 g of 1,3,5-tris-(5-hydroxy-1-pentynyl)-benzene. Yield: 74%. 1H NMR (300 MHz, CDCl3) δ 7.31 (3, 3h), 3.81 (t, J=6.0 Hz, 6H), 2.52 (t, J=6.9 Hz, 6H), 1.85 (m, 6H); 13C NMR (75 MHz, CDCl3) δ 133.8, 124.2, 90.5, 80.0, 61.9, 31.5, 16.2 ppm.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a celite pad
  3. washrinsed with ethyl acetate
  4. customThe combined filtrate was evaporated to dryness under reduced pressure
  5. customThe resulting residue was purified by column chromatography (CHCl3:MeOH 10:1)

Sources & evidence

ORD record
ord-09562f1db5ae4e73a66e6fe54197a605
Source dataset
uspto-grants-2014_04
Patent number
US08703803B2

Reaction notes

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