2-Fluoroethanol → HCID 15058773, compound

HRID 1087900Notes

Reaction equation

HRID 1087900 reaction equation
[Na].[F:2][CH2:3][CH2:4][OH:5].Br[CH2:7][C:8]1[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:12][CH:13]=1>O1CCCC1.O>[N+:14]([C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][O:5][CH2:4][CH2:3][F:2])([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 97372-FluoroethanolHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 5360545Sodium2×

Product 1

HCID 15058773HCID 15058773, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a dry nitrogen atmosphere 1.1 gram (0.047 mole) of sodium metal was added to a stirred, cold (0° C.) solution of 3.0 grams (0.046 mole) of 2-fluoroethanol in 50 ml of dry tetrahydrofuran. After the sodium had dissolved, the solution was heated at reflux, and a solution of 5.0 grams (0.023 mole) of 3-bromomethylnitrobenzene in 10 ml of dry tetrahydrofuran was added dropwise. This mixture was heated at reflux for 24 hours and then was cooled. The reaction mixture was diluted with water, then was extracted with diethyl ether. The organic extract was washed with an aqueous, saturated, sodium chloride solution. The washed extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving a residue. This residue was purified by column chromatography on silica gel, eluting with n-hexane:diethyl ether (4:1), to yield 0.8 gram of 2-fluoroethyl 3-nitrobenzyl ether as an oil.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux
  3. temperatureThis mixture was heated
  4. temperatureat reflux for 24 hours
  5. temperaturewas cooled
  6. extractionwas extracted with diethyl ether
  7. extractionThe organic extract
  8. washwas washed with an aqueous, saturated, sodium chloride solution
  9. extractionThe washed extract
  10. dry with materialwas dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customThe filtrate was evaporated under reduced pressure
  13. customleaving a residue
  14. customThis residue was purified by column chromatography on silica gel
  15. washeluting with n-hexane:diethyl ether (4:1)

Sources & evidence

ORD record
ord-dbd64b29d8914440bee9b78843ad120a
Source dataset
uspto-grants-1990_10
Patent number
US04960884

Reaction notes

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