Trimethyl phosphite → Dimethyl[4-(phenylsulfonyl)benzyl]phosphonate

HRID 2376967

Reaktionsgleichung

Reaktionsgleichung von HRID 2376967
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:18][O:19][P:20]([O:23]C)[O:21][CH3:22]>>[CH3:18][O:19][P:20]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)(=[O:23])[O:21][CH3:22]

Komponenten

3

Edukt 2

HCID 8472Trimethyl phosphiteHCID 2641001-(Bromomethyl)-4-(phenylsulfonyl)benzene

Produkt 1

HCID 15247537Dimethyl[4-(phenylsulfonyl)benzyl]phosphonateAusbeute 86 %

Versuchsvorschrift

1-(Bromomethyl)-4-(phenylsulfonyl)benzene (Step 1, 10.1 g, 32.5 mmol) was heated to reflux in trimethylphosphite (40 mL) for 16 hours. The cooled reaction was azeotroped with xylene then purified by flash column chromatography on silica, eluting with ethyl acetate to give dimethyl[4-(phenylsulfonyl)benzyl]phosphonate (9.5 g, 86%). δH (360 z, CDCl3): 7.92-7.84 (4H, m), 7.55-7.39 (5H, m), 3.64 (6H, d, J=10.9 Hz), 3.16 (2H, d, J=21.6 Hz).

Aufarbeitung

  1. customThe cooled reaction
  2. customwas azeotroped with xylene
  3. customthen purified by flash column chromatography on silica
  4. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1d515866fa3f4f189436ab1cecfeeae2
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468393B2

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