1,3-Dibromobenzene → HCID 58338519, compound

HRID 1925452Notes

Reaction equation

HRID 1925452 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[CH:3]=1.[CH2:9]([OH:14])[CH2:10][CH2:11][C:12]#[CH:13]>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:14][CH2:9][CH2:10][CH2:11][C:12]#[C:13][C:4]1[CH:3]=[C:2]([C:13]#[C:12][CH2:11][CH2:10][CH2:9][OH:14])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 79271,3-DibromobenzeneHCID 793464-Pentyn-1-ol

Product 1

HCID 58338519HCID 58338519, compoundYield 94.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
75 °C

Procedure

1,3-Dibromobenzene (7.48 g, 31.71 mmol), 4-pentyn-1-ol (6.40 g, 76.10 mmol), and bis(triphenylphosphine)palladium(II) dichloride (445 mg, 0.63 mmol) was stirred in triethylamine (150 mL) under nitrogen for 5 min. Copper(I) iodide (61 mg, 0.32 mmol) was added and the mixture was stirred for 18 hrs at 75° C. The mixture was cooled to room temperature and filtered through a celite pad, rinsed with ethylacetate. The combined filtrate was evaporated to dryness under reduced pressure. The resulting residue was purified by column chromatography (chloroform:methanol 20:1) to afford 7.24 g of the title compound. Yield: 94%. 1H NMR (300 MHz, CDCl3) δ 1.85 (m, 4H), 2.53 (t, J=6.9 Hz, 4H), 3.81 (t, J=6.0 Hz, 4H), 7.16-7.31 (m, 3H), 7.42 (t, J=1.2 Hz, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 16.2, 31.6, 61.9, 80.6, 90.0, 124.0, 128.3, 130.8, 134.7 ppm.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a celite pad
  3. washrinsed with ethylacetate
  4. customThe combined filtrate was evaporated to dryness under reduced pressure
  5. customThe resulting residue was purified by column chromatography (chloroform:methanol 20:1)

Sources & evidence

ORD record
ord-1828e757c21e4e4ea44898e8d4402748
Source dataset
uspto-grants-2012_05
Patent number
US08178678B2

Reaction notes

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