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

HRID 1351652

Reaktionsgleichung

Reaktionsgleichung von HRID 1351652
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]>>[C:12]1([S:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][P:20](=[O:23])([O:21][CH3:22])[O:19][CH3:18])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

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 MHz, 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-263a52b89f07446ba3e970fb9cc93960
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217740B2

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