Iodoethane → HCID 21829131, compound

HRID 2374175Notes

Reaction equation

HRID 2374175 reaction equation
I[CH2:2]C.[N+:4]([C:7]1[CH:8]=[C:9](O)[C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)([O-:6])=[O:5].[C:16]([O-:19])([O-])=O.[K+].[K+]>CN(C=O)C.O.C(OC)(C)(C)C>[CH2:14]([O:13][C:10]1[CH:9]=[CH:8][C:7]([N+:4]([O-:6])=[O:5])=[CH:12][C:11]=1[O:19][CH3:16])[CH3:2]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 21829131HCID 21829131, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Iodoethane (1.93 mL, 38.4 mmol) was added dropwise over 15 min. to a stirred mixture of 4-nitroguaiacol 1 (5.00 g, 29.6 mmol) and K2CO3 (6.21 g, 44.3 mmol) in DMF (30 ml) at 60° C. under nitrogen. After 2 h the reaction was cooled to RT and diluted with water (100 ml) and methyl tert-butyl ether (250 ml). The organic layer was washed with water (25 ml), brine (2×20 ml), dried over Na2SO4, filtered and concentrated under vacuum to afford 2-ethoxy-5-nitroanisole (5.74 g) as a pale yellow solid. mp 88-90° C. 1H NMR (DMSO-d6) δ 7.89 (dd, 1H), 7.73 (d, 1H), 7.16 (d, 1H), 4.17 (q, 2H), 3.88 (s, 3H), 1.37 (t, 3H). 13C NMR (DMSO-d6) δ 153.9, 148.6, 140.5, 117.6, 111.5, 106.4, 64.6, 55.9, 14.4. MS (ESI+) for m/z 198 [M+H]+.

Workup

  1. washThe organic layer was washed with water (25 ml), brine (2×20 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5403b42ed874434491329ba621452c8b
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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