2-Methyl-3-butyn-2-ol → 4-(3,5-Dichloro-phenyl)-2-methyl-but-3-yn-2-ol

HRID 1199081Notes

Reaction equation

HRID 1199081 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(CC)CC)C.[CH3:17][C:18]([OH:22])([C:20]#[CH:21])[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:21]#[C:20][C:18]([CH3:19])([OH:22])[CH3:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 764241,3-Dichloro-5-iodobenzene

Product 1

HCID 138235464-(3,5-Dichloro-phenyl)-2-methyl-but-3-yn-2-ol

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 25.5 g (0.094 mole) of 3,5-dichloroiodobenzene, 550 ml dry triethylamine, 12 g (0.14 mole) of 2-methyl-2-hydroxy-3-butyne, 0.42 g (0.0019 mole) palladium (II) acetate, and 1 g (0.0038 mole) of triphenylphosphine was heated to reflux under nitrogen for four hours. The resulting mixture was cooled, diluted with ether and washed with two 500-ml portions of 3N hydrochloric acid. The ether layer was separated, dried over anhydrous magnesium sulfate, and evaporated in vacuo to yield the crude product as an oily residue. The purified product was obtained by distillation to yield 7.95 g, bp 115°-125° C./0.0001 mm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for four hours
  3. temperatureThe resulting mixture was cooled
  4. washwashed with two 500-ml portions of 3N hydrochloric acid
  5. customThe ether layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-07bda36d6cd346e292689e56b052678e
Source dataset
uspto-grants-1990_02
Patent number
US04898889

Reaction notes

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