Water → HCID 11961624, compound

HRID 2223758Notes

Reaction equation

HRID 2223758 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([O:7][C:8]1[C:9]([F:21])=[C:10]([C:13]([CH2:19]O)=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[C:11]#[N:12])[CH3:6].C(OCC)(=O)C.O>COCCOC>[Br:2][CH2:19][C:13]1[C:10]([C:11]#[N:12])=[C:9]([F:21])[C:8]([O:7][CH2:5][CH3:6])=[C:15]([O:16][CH2:17][CH3:18])[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24614Phosphorus tribromideHCID 23093714HCID 23093714, compound

Product 1

HCID 11961624HCID 11961624, compoundYield 180.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Phosphorus tribromide (PBr3, 1.57 mL, 16.7 mmol) was added to a solution of 3,4-diethoxy-2-fluoro-6-(hydroxymethyl)benzonitrile (38.0 g, 33.4 mmol) in 1,2-dimethoxyethane (DME) (80 mL) on ice, followed by 3 hours of stirring at room temperature. After the reaction solution was cooled on ice, ethyl acetate and water were added. The organic layer was separated, and the aqueous layer was extracted further with ethyl acetate. The combined extract solutions were washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and after addition of activated charcoal, were dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off, followed by addition of n-heptane (100 mL) to the residue, and the solvent was distilled off again. n-Heptane (100 mL) was added to the residue, and this was cooled on ice. Precipitated crystals were collected by filtration, and washed with n-heptane to give 9.1 g of the subject compound (yield: 90.1%).

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted further with ethyl acetate
  4. extractionThe combined extract solutions
  5. washwere washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. additionafter addition of activated charcoal
  7. dry with materialwere dried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off
  10. additionfollowed by addition of n-heptane (100 mL) to the residue
  11. distillationthe solvent was distilled off again
  12. additionn-Heptane (100 mL) was added to the residue
  13. temperaturethis was cooled on ice
  14. customPrecipitated crystals
  15. filtrationwere collected by filtration
  16. washwashed with n-heptane

Sources & evidence

ORD record
ord-43ce27307ef94ace9289c6bd2256570a
Source dataset
uspto-grants-2008_05
Patent number
US07375236B2

Reaction notes

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