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

HRID 1351652

反応式

HRID 1351652 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]>>[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

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 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).

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-263a52b89f07446ba3e970fb9cc93960
出典データセット
uspto-grants-2007_05
特許番号
US07217740B2

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