Benzene, 1-bromo-3-iodo- → 4-(3-Bromophenyl)but-3-yn-1-ol

HRID 2117665Notes

Reaction equation

HRID 2117665 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[CH2:9]([OH:13])[CH2:10][C:11]#[CH:12]>C(#N)C.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[C:4]([C:12]#[C:11][CH2:10][CH2:9][OH:13])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11561Benzene, 1-bromo-3-iodo-HCID 135663-Butyn-1-OL

Product 1

HCID 218954424-(3-Bromophenyl)but-3-yn-1-ol

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A stirred, cooled solution of 1-bromo-3-iodobenzene (31 g) and 3-butyn-ol (7 ml) in acetonitrile (100 ml) and triethylamine (100 ml) was purged with nitrogen for 20 min under nitrogen. Dichlorobis(triphenylphosphine)palladium (500 mg) and cuprous iodide (800 mg) were added. The mixture was stirred for 18 h and then the solvent was removed in-vacuo. The residual oil was triturated with ethyl acetate (200 ml) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on Biotage (90 g) eluting with light petroleum 40-60°-diethyl ether (3:2) to give the title compound (21 g). LCMS RT=3.26 min.

Workup

  1. customwas purged with nitrogen for 20 min under nitrogen
  2. additionDichlorobis(triphenylphosphine)palladium (500 mg) and cuprous iodide (800 mg) were added
  3. customthe solvent was removed in-vacuo
  4. customThe residual oil was triturated with ethyl acetate (200 ml)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on Biotage (90 g)
  8. washeluting with light petroleum 40-60°-diethyl ether (3:2)

Sources & evidence

ORD record
ord-5f70cedc2e5e4492b86cb1e363c598eb
Source dataset
uspto-grants-2008_10
Patent number
US07442719B2

Reaction notes

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