Dimethylformamide → HCID 22718330, compound

HRID 1582749Notes

Reaction equation

HRID 1582749 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]([CH:13]1[O:15][CH2:14]1)Br.CN(C)C=[O:19]>>[CH2:11]([O:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:13]1[O:15][CH2:14]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 97324-FluorophenolHCID 18430EpibromohydrinHCID 24758Sodium hydride

Product 1

HCID 22718330HCID 22718330, compoundYield 75%

Procedure

4-Fluorophenol (3.0 g) was dissolved in dimethylformamide (50 ml), then sodium hydride (1.28 g, 50%) was added thereto, and the mixture was stirred for 45 minutes in an ice bath. Epibromohydrin (2.3 ml) was added to the reaction mixture, and the mixture was stirred for 3 hours in the ice bath. The organic layer was partitioned by adding water and diethyl ether, and the resulting organic layer was washed with water and brine, dried, and evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the free compound (3.4 g, 75%) of the title compound as a colorless oil.

Workup

  1. customThe organic layer was partitioned
  2. additionby adding water and diethyl ether
  3. washthe resulting organic layer was washed with water and brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-c7225444e361492eb1cd10d03db87f17
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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