Diethyl Sulfate → 4-Ethoxy-2-fluoronitrobenzene

HRID 537301Notes

Reaction equation

HRID 537301 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].S(OCC)(O[CH2:16][CH3:17])(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:16]([O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1)[CH3:17]

Participants

6

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 135386514-Ethoxy-2-fluoronitrobenzeneYield 98.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-fluoro-4-nitrophenol (9.9 g, 0.063 mol) and diethyl sulfate (12.17 g, 0.079 mol) in DMF (100 mL) was added K2CO3 (17.39 g, 0.126 mol). The resulting mixture was stirred at 80° C. for 90 min and then cooled to rt. The reaction mixture was diluted with H2O (200 mL) and extracted with 25% EtOAc in hexanes (2×100 mL). The combined organic phases were washed with brine (100 mL), filtered through phase separation filter paper, and concentrated in vacuo to give 11.5 g (98%) of 53 as an orange-yellow solid. 1H NMR (60 MHz, CDCl3): δ 8.8-7.7 (m, 1H), 6.6-6.2 (m, 2H), 4.0 (q, 2H), 1.4 (t, 3H) ppm.

Workup

  1. temperaturecooled to rt
  2. extractionextracted with 25% EtOAc in hexanes (2×100 mL)
  3. washThe combined organic phases were washed with brine (100 mL)
  4. filtrationfiltered through phase separation
  5. filtrationfilter paper
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed9a89b27fac45a2b7a8b3b878b0f0db
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

Loading…