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

HRID 2376967Notes

Reaction equation

HRID 2376967 reaction equation
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]

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-1d515866fa3f4f189436ab1cecfeeae2
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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