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

HRID 2376967

反応式

HRID 2376967 の反応式
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]

参加物

3

反応物 2

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

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1d515866fa3f4f189436ab1cecfeeae2
出典データセット
uspto-grants-2008_12
特許番号
US07468393B2

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