Tetrahydrofuran → HCID 66832323, compound

HRID 562415Notes

Reaction equation

HRID 562415 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](Cl)(Cl)=[O:9])=[CH:4][CH:3]=1.[CH:12]([Mg]Br)=[CH2:13].[Cl-].[NH4+].[CH2:18]1COC[CH2:19]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](=[O:9])([CH:12]=[CH2:13])[CH:18]=[CH2:19])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 12670632(4-Fluorophenyl)phosphonic dichlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 66832323HCID 66832323, compoundYield 83%

Conditions

Temperature
-70 °C

Procedure

4-Fluorophenyl-phosphonic dichloride (6.86 g, 32.2 mmol) was dissolved in dry THF (50 mL), placed under a nitrogen atmosphere, and chilled to −70° C. To this stirred solution was added dropwise a solution of vinyl magnesium bromide in THF (80.5 mL, 1M). The resulting solution was stirred for 90 minutes at −70° C. An aqueous solution of ammonium chloride (500 mL, 2M) was chilled to 0° C. and stirred rapidly while the cold reaction mixture was added. The product was extracted into dichloromethane and washed with saturated aqueous sodium bicarbonate followed by water. The organic phase was dried with sodium sulfate, filtered, and concentrated by rotary evaporation to yield 5.214 g of 4-fluoro-phenyl-divinyl-phosphine oxide (26.6 mmol, 83%) as a white solid. 1H NMR (400 MHz, CDCl3) 7.80-7.71 (m, 2H); 7.25-7.18 (m 2H); 6.56-6.22 (m, 6H); ESMS (m/z): (M+1)+ found, 197.

Workup

  1. stirringstirred rapidly while the cold reaction mixture
  2. additionwas added
  3. extractionThe product was extracted into dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-d336d5d68b4c4907a03c4ece191ebd93
Source dataset
uspto-grants-2011_11
Patent number
US08067395B2

Reaction notes

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