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

HRID 1351652Notes

Reaction equation

HRID 1351652 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]>>[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

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 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).

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-263a52b89f07446ba3e970fb9cc93960
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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