4-Fluorophenol → HCID 70654247, compound

HRID 1403334Notes

Reaction equation

HRID 1403334 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[H][H].[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])CBr)[CH3:14]>CN(C)C=O>[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[O:10][C:7]1[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=1)[CH3:14]

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 178418361HCID 178418361, compound

Product 1

HCID 70654247HCID 70654247, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of sodium hydride (11.24 g, 281.00 mmol) in anhydrous N,N-dimethylformamide (500 mL) was added 4-fluorophenol (26.21 g, 233.96 mmol) at 0° C. After hydrogen evolution had ceased, bromo-acetaldehyde diethyl acetal (55 g, 280.60 mmol) was added. The reaction was heated at 120° C. overnight. The mixture was poured into ice-water, extracted with ethyl acetate (3×150 mL), washed with 1N sodium hydroxide (3×100 mL), and brine (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to give the residue, which was purified by a silica gel column with 1% ethyl acetate in petroleum ether to afford 1-(diethoxymethoxy)-4-fluorobenzene as oil (45 g, 84%).

Workup

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washwashed with 1N sodium hydroxide (3×100 mL), and brine (3×100 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under vacuum
  6. customto give the residue, which
  7. customwas purified by a silica gel column with 1% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-ff391bc8a8b349a5a0f8feabc82546a0
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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