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Propargyl alcohol → 3-(3-Bromophenyl)prop-2-yn-1-ol

HRID 1093373
Notes
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Reaction equation

HRID 1093373 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:28]([OH:31])[C:29]#[CH:30].C(N(C(C)C)CC)(C)C>[Cl-].[Na+].O.[Cu]I.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:30]#[C:29][CH2:28][OH:31])[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 7859Propargyl alcoholHCID 11561Benzene, 1-bromo-3-iodo-HCID 11776TriphenylphosphineHCID 81531Diisopropylethylamine

Product 1

HCID 36456413-(3-Bromophenyl)prop-2-yn-1-ol

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)Catalyst
HCID 8028TetrahydrofuranSolvent
HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 3-bromoiodobenzene (5.00 g), copper(I) iodide (67.4 mg), triphenylphosphine (232 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (366 mg), propargyl alcohol (1.15 ml), diisopropylethylamine (12.3 ml) and tetrahydrofuran (90 ml) was stirred at room temperature for 15 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=98:2-70:30) to give the object product (3.42 g) as a brown oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=98:2-70:30)

Sources & evidence

ORD record
ord-6dd0f60c459a4ff79565fdf7f1d055d6
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129361B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes