Tetrahydrofuran → 1-Bromo-3-(prop-1-yn-1-yl)benzene

HRID 539281Notes

Reaction equation

HRID 539281 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.C[Si](C)(C)[C:11]#[C:12][CH3:13].C(N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>C1(C)C=CC=CC=1.[Cu]I.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>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:11]#[C:12][CH3:13])[CH:3]=1

Participants

9

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11561Benzene, 1-bromo-3-iodo-HCID 803631-(Trimethylsilyl)prop-1-yneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 691818821-Bromo-3-(prop-1-yn-1-yl)benzeneYield 80%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 1-bromo-3-iodobenzene (3.0 g, 10.6 mmol), copper(I) iodide (0.61 g, 3.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.61 g, 0.53 mmol) in toluene (20 mL) was added 1-(trimethylsilyl)-1-propyne (1.6 mL, 10.6 mmol), triethylamine (4.9 mL, 35.0 mmol) and a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (10.6 mL, 10.6 mmol). The resulting mixture was stirred under a nitrogen atmosphere at r.t. overnight. The mixture was partitioned between water and Et2O and the organic phase was dried over magnesium sulfate and concentrated in vacuo. The residue was filtered through a plug of silica and eluted with heptane (4×25 mL) affording the title compound (1.6 g, 80% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 2.05 (s, 3H), 7.30 (t, 1H), 7.39 (d, 1H), 7.52-7.56 (m, 1H), 7.56-7.58 (m, 1H); MS (CI) m/z 195 [M+H]+.

Workup

  1. customThe mixture was partitioned between water and Et2O
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. filtrationThe residue was filtered through a plug of silica
  5. washeluted with heptane (4×25 mL)

Sources & evidence

ORD record
ord-d4955cba375a425cb33d723163f45b75
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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