Sodium hydride → 2-(2-Fluoroethoxy)-dibenzofuran

HRID 1086012

Reaction equation

HRID 1086012 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:16]=[CH:15][C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1.CS(O[CH2:22][CH2:23][F:24])(=O)=O>CN(C)C=O>[F:24][CH2:23][CH2:22][O:3][C:4]1[CH:16]=[CH:15][C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 665872-DibenzofuranolHCID 680342-Fluoroethyl methanesulfonate

Product 1

HCID 156713922-(2-Fluoroethoxy)-dibenzofuranYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% oil dispersion; 4.0 g) in N,N-dimethylformamide (100 ml), 2-hydroxydibenzofuran (18.4 g) was added at a temperature of 0 to 5° C., and the resultant suspension was stirred at room temperature for 1 hour. 2-Fluoroethyl methanesulfonate (14.2 g) was added thereto. The resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with aqueous potassium carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was distilled under reduced pressure to give 2-(2-fluoroethoxy)-dibenzofuran (Compound No. 35) (19.6 g). b.p., 180°-185° C./5 mmHg.

Workup

  1. additionwas added at a temperature of 0 to 5° C.
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with aqueous potassium carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-aaed0e6cf14c482d99a5ef2f44a1e247
Source dataset
uspto-grants-1991_04
Patent number
US05012004

Linked notes

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