Triethylamine → E-5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]benzaldehyde

HRID 1672630Notes

Reaction equation

HRID 1672630 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH2:18])=[CH:15][CH:14]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:10][C:7]1[CH:8]=[CH:9][C:2](/[CH:18]=[CH:17]/[C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 125074-MethoxystyreneHCID 80271Tri-o-tolylphosphineHCID 27733212-Bromo-5-fluorobenzaldehyde

Product 1

HCID 57831341E-5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]benzaldehydeYield 61.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 10 g (49.26 mmol) of 2-bromo-5-fluorobenzaldehyde in 200 ml of dry DMF is mixed with 7.27 g (54.18 mmol) of 4-methoxystyrene, 1.5 g (4.93 mmol) of tri-2-tolylphosphine, 330 mg (1.48 mmol) of palladium(II) acetate and 10.3 ml (73.89 mmol) of triethylamine under argon and stirred at 100° C. for 12 hours. After reaction is complete, the reaction solution is cooled to room temperature and concentrated to dryness. The resulting residue is taken up in 100 ml of water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases are dried over sodium sulfate. After filtration, the solution is concentrated to dryness, and the residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 7.79 g (55% yield) of a colorless solid are obtained.

Workup

  1. customAfter reaction
  2. temperaturethe reaction solution is cooled to room temperature
  3. concentrationconcentrated to dryness
  4. extractionextracted three times with 50 ml of diethyl ether each time
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe solution is concentrated to dryness
  8. customthe residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-b7534bb800864722a5100566d95dfcbb
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

Loading…