1,2-Dibromobenzene → HCID 13978687, compound

HRID 1925450Notes

Reaction equation

HRID 1925450 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1Br.[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:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:13]#[C:12][CH2:11][CH2:10][CH2:9][OH:14]

Participants

6

Reactant 2

HCID 114141,2-DibromobenzeneHCID 793464-Pentyn-1-ol

Product 1

HCID 13978687HCID 13978687, compoundYield 47.4%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
85 °C

Procedure

1,2-Dibromobenzene (10.94 g, 46.37 mmol), 4-pentyn-1-ol (9.36 g, 111.30 mmol), and bis(triphenylphosphine)palladium(II) dichloride (650 mg, 0.93 mmol) was stirred in triethylamine (150 mL) under nitrogen for 5 min. Copper(I) iodide (88 mg, 0.46 mmol) was added and the mixture was stirred for 4 hrs at 85° C. for 6 days. 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 30:1) to afford 5.33 g of the title compound. Yield: 47%. 1H NMR (300 MHz, D2O) δ 1.85 (m, 4H), 2.58 (t, J=6.6 Hz, 4H), 3.82 (t, J=6.0 Hz, 4H), 7.18 (m, 2H), 7.36 (m, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 16.3, 31.4, 62.4, 80.2, 93.3, 126.0, 127.4, 131.8 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 30:1)

Sources & evidence

ORD record
ord-ea2ce802614a4485b61e070020b37f6d
Source dataset
uspto-grants-2012_05
Patent number
US08178678B2

Reaction notes

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