Phenol → HCID 69310862, compound

HRID 1593765Notes

Reaction equation

HRID 1593765 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH3:12][O:13][CH2:14][CH2:15]Cl.C(=O)([O-])[O-].[K+].[K+].C1(O)C=CC=CC=1>CN(C)C=O.[I-].[Na+]>[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:15][CH2:14][O:13][CH3:12]

Participants

7

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl ether2×HCID 2849492-iodo-4-nitrophenol

Product 1

HCID 69310862HCID 69310862, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-iodo-4-nitrophenol (15.5 g, 58.7 mmol) [ref: Kometani, T.; Watt, D. S.; Ji, T., Tetrahedron Lett. (1985), 26(17), 2043], 2-chloroethyl methyl ether (10.69 mL, 117 mmols), potassium carbonate (16.8 g, 117 mmol) and sodium iodide (100 mg) in 160 mL of N,N-dimethylformamide was heated at 70-80° C. for 4 hours. An additional 5.35 mL of 2-chloroethyl methyl ether was added and the reaction was heated until thin layer chromatography (TLC) showed the absence of the phenol. The mixture was filtered and the filtrate was concentrated in vacuo. The solid was partitioned between ethyl acetate and 1 N sodium hydroxide. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a gradient of hexane to 50% ethyl acetate in hexane. The resultant oil was recrystallized from ether to provide 7.5 g of 2-iodo-1-(2-methoxyethoxy)-4-nitrobenzene as a white solid, mp 35-36° C.; 1H NMR (300 MHz, DMSO-d6) δ 3.37 (s, 3H), 3.74 (t, 2H), 4.33 (t, 2H), 7.20 (d, 1H), 8.26 (d, 1H), 8.56 (s, 1H)

Workup

  1. temperaturethe reaction was heated until thin layer chromatography (TLC)
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe solid was partitioned between ethyl acetate and 1 N sodium hydroxide
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluting with a gradient of hexane to 50% ethyl acetate in hexane
  10. customThe resultant oil was recrystallized from ether

Sources & evidence

ORD record
ord-56ef54843a844fd7a2f4983e62510535
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

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