Tetrahydrofuran → HCID 59635639, compound

HRID 454806Notes

Reaction equation

HRID 454806 reaction equation
[F:1][CH2:2][CH2:3][OH:4].O1CCCC1.[H-].[Na+].[Br:12][C:13]1[CH:14]=[CH:15][C:16](Cl)=[N:17][CH:18]=1>O>[F:1][CH2:2][CH2:3][O:4][C:16]1[CH:15]=[CH:14][C:13]([Br:12])=[CH:18][N:17]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 97372-FluoroethanolHCID 24758Sodium hydrideHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 59635639HCID 59635639, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Fluoroethanol (259 mg, 3.90 mmol) was added to a solution of anhydrous tetrahydrofuran (10 mL) containing sodium hydride (NaH 60%, 94 mg, 3.90 mmol) under nitrogen, stirred for 5 minutes, and 5-bromo-2-chloropyridine (96, 500 mg, 2.59 mmol) was added thereto and stirred at room temperature for 3 hours. Water was added to the reaction mixture and organic compounds were extracted with ethyl acetate and evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give the target compound 2-(2-fluoroethoxy)-5-bromopyridine (97b, 230 mg, 40%).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. extractionwere extracted with ethyl acetate
  3. customevaporated after a treatment with sodium sulfate
  4. customPurification

Sources & evidence

ORD record
ord-63c7c74f73ef4d7fb155eb1c0855a1e4
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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