Tetrahydrofuran → HCID 66832446, compound

HRID 562404Notes

Reaction equation

HRID 562404 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][P:7](Cl)(Cl)=[O:8])=[CH:4][CH:3]=1.[CH:13]([Mg]Br)=[CH2:14].[Cl-].[NH4+].[CH2:19]1COC[CH2:20]1>>[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][P:7](=[O:8])([CH:13]=[CH2:14])[CH:19]=[CH2:20])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 86618279HCID 86618279, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 66832446HCID 66832446, compoundYield 84%

Conditions

Temperature
-70 °C

Procedure

4-Fluorobenzyl phosphonic dichloride (1.71 g, 7.82 mmol) was dissolved in 10 mL of dry THF, under a nitrogen atmosphere, and chilled to −70° C. To this stirred solution was added dropwise vinyl magnesium bromide in THF (18.3 mL, 1M). The resulting solution was stirred for 30 minutes at −70° C. An aqueous solution of ammonium chloride (100 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, and then with water. The organic phase was dried with sodium sulfate, filtered, and concentrated by rotary evaporation to yield 1.375 g of (4-fluorophenylmethyl) divinyl phosphine oxide (6.55 mmol, 84%) as a white solid. 1H NMR (400 MHz, CDCl3) 7.20-7.14 (m, 2H); 7.01-6.95 (m 2H); 6.29-6.08 (m, 6H); 3.20-3.15 (d, 2H); ESMS (m/z): (M+1)+ found, 211.

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-33a631ccf00d4047a1cdefa43599ade3
Source dataset
uspto-grants-2011_11
Patent number
US08067395B2

Reaction notes

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