1-Butyne → HCID 118022026, compound

HRID 575837Notes

Reaction equation

HRID 575837 reaction equation
I[C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[C:4]([I:12])[C:3]=1[OH:13].[CH:14]#[C:15][CH2:16][CH3:17]>N1C=CC=CC=1.Cl>[CH2:16]([C:15]1[O:13][C:3]2[C:4]([I:12])=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=2[CH:14]=1)[CH3:17]

Participants

5

Reactant 2

HCID 78461-ButyneHCID 49857092,6-Diiodo-4-(methanesulfonyl)phenol

Product 1

HCID 118022026HCID 118022026, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2,6-diiodo-4-methylsulfonylphenol (1.00 g, 2.36 mmol) in pyridine (10 mL) at 25° C. was added but-1-yne (128 mg, 2.36 mmol) and Cu2O (135 mg, 0.944 mmol). The mixture was stirred at 130° C. for 3 h under a nitrogen atmosphere. The residue was cooled to 25° C., diluted with 1N HCl (200 ml) and extracted with EtOAc (30 mL×2). The combined organic layers were washed by brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (PE:EA=10:1 to 5:1) to afford the title compound (400 mg, 48%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 8.14 (d, J=1.6 Hz, 1H), 8.06 (d, J=1.6 Hz, 1H), 6.62 (s, 1H), 3.09 (s, 3H), 2.90 (q, J=7.6 Hz, 2H), 1.38 (t, J=7.6 Hz, 3H). LCMS: 350.9 (M+H+)

Workup

  1. temperatureThe residue was cooled to 25° C.
  2. extractionextracted with EtOAc (30 mL×2)
  3. washThe combined organic layers were washed by brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (PE:EA=10:1 to 5:1)

Sources & evidence

ORD record
ord-975c7111425646ceb92bdee7ba46b225
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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