Ethyl Bromide → 1-Ethoxy-2,5-difluoro-4-nitrobenzene

HRID 1811549Notes

Reaction equation

HRID 1811549 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+].Br[CH2:20][CH3:21].ICC>C(#N)C>[CH2:20]([O:12][C:3]1[CH:4]=[C:5]([F:11])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1])[CH3:21]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27824902,5-Difluoro-4-nitrophenol

Product 1

HCID 685658171-Ethoxy-2,5-difluoro-4-nitrobenzeneYield 88.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2,5-difluoro-4-nitro-phenol (4.86 g, 28.2 mmol) in acetonitrile (50 mL), potassium carbonate (4.7 g, 34 mmol) and bromoethane (4.21 mL, 56.4 mmol) were added. After stirring at 70° C. for 3.5 hours, iodoethane (2.73, 33.8 mmol) was added and mixture was stirred at 80° C. After 20 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-ethoxy-2,5-difluoro-4-nitro-benzene as a yellow solid (5.05 g, 88%). 1HNMR (CDCl3, 400 MHz) δ 7.92-7.88 (m, 1H), 6.82-6.78 (m, 1H), 4.21-4.16 (q, 1H), 4.13-4.07 (q, J=7.0 Hz, 2H), 1.54-1.51 (t, J=7.0 Hz, 3H).

Workup

  1. stirringmixture was stirred at 80° C
  2. waitAfter 20 hours
  3. concentrationmixture was concentrated
  4. extractionextracted with methylene chloride and 2M NaOH solution
  5. dry with materialOrganic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-286ff2a7d1a84cddbf78d767383003a3
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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