Potassium Carbonate → 1,4-Difluoro-2-nitro-5-propoxybenzene

HRID 1811548Notes

Reaction equation

HRID 1811548 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH2:21][CH3:22]>C(#N)C>[F:11][C:5]1[CH:4]=[C:3]([O:12][CH2:20][CH2:21][CH3:22])[C:2]([F:1])=[CH:7][C:6]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 27824902,5-Difluoro-4-nitrophenol

Product 1

HCID 685663551,4-Difluoro-2-nitro-5-propoxybenzeneYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,5-difluoro-4-nitro-phenol (1.71 g, 9.77 mmol) in acetonitrile (20 mL), potassium carbonate (2.7 g, 19.5 mmol) and 1-iodopropane (1.14 mL, 11.7 mmol) were added. After stirring at 60° C. for 15 hours, mixture was concentrated and extracted with methylene chloride and 2M NaOH solution. Organic phases were dried over magnesium sulfate, filtered, and concentrated to give 1,4-difluoro-2-nitro-5-propoxy-benzene as a yellow solid (0.995 g, 47%). 1HNMR (CDCl3, 400 MHz) δ 7.92-7.88 (m, 1H), 6.83-6.78 (m, 1H), 4.08-4.05 (t, J=6.5 Hz, 2H), 1.95-1.86 (m, 2H), 1.10-1.06 (t, J=7.4 Hz, 2H).

Workup

  1. concentrationmixture was concentrated
  2. extractionextracted with methylene chloride and 2M NaOH solution
  3. dry with materialOrganic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0fb40bbc96714c8181cd2d8623ade33a
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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