Dimethylformamide → 3-(2,4,6-Trichloro-phenyl)-prop-2-yn-1-ol

HRID 1039351Notes

Reaction equation

[CH2:1]([OH:4])[C:2]#[CH:3].[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:7]=1I.CN(C)C=O.C(N(CC)CC)C>[Cl-].[Na+].O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu](I)I>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:7]=1[C:3]#[C:2][CH2:1][OH:4]

Participants

Conditions

Temperature: 120 °C

Procedure

To a microwave vial were added propargyl alcohol (0.19 ml; 3.3 mmol), 1,3,5-trichloro-2-iodo-benzene (0.50 g; 1.6 mmol), N,N-dimethylformamide (6 ml), triethylamine (4 ml), bis(triphenylphosphine) palladium(II) chloride (0.11 g; 0.16 mmol) and copper iodide (31 mg; 0.16 mmol). The mixture was degassed under argon. The orange solution was heated in the microwave at 120° C. during 25 min. The mixture obtained was poured in brine and extracted three times with dichloromethane. Organic were combined, dried over sodium sulfate and evaporated under reduced pressure to provide the crude which was subject to flash chromatography (eluant: c-hexane/ethyl acetate 8:2). 290 mg (75% of theory) of 3-(2,4,6-trichloro-phenyl)-prop-2-yn-1-ol was obtained as a yellow solid.

Workup

customThe mixture was degassed under argon
customThe mixture obtained
extractionextracted three times with dichloromethane
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
customto provide the crude which

Sources & evidence

ORD record: ord-a242337a48714ba7ac3e8fa65a370d5b
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552049B2

Reaction notes

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