Thionyl Chloride → 4-Phenoxybenzene-1-sulfonyl chloride

HRID 37739

反応式

HRID 37739 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([OH:17])(=O)=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>CN(C=O)C>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([Cl:20])(=[O:17])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 110815014-phenoxybenzenesulfonic Acid

生成物 1

HCID 27947564-Phenoxybenzene-1-sulfonyl chloride

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The sulphonic acid (2a) was dissolved in an excess of thionyl chloride (30 mL), a catalytic amount of DMF (cat) was added, and the resulting mixture was stirred for 6 h at reflux. The solvent was evaporated and the residue dissolved in Et20 (40 mL). The ether solution was washed with 5% aqueous NaOH (3×40 mL) and water (6×40 mL), dried over anhydrous MgSO4, filtered, and concentrated in vacuo. After drying in high vacuum overnight, the pure product was obtained as a white solid. Yield 63%: 2.09 g, 7.44 mmol, (light yellow syrup). 1H-NMR (CDCl3): δ 7.44 (d, 3J=9.1 Hz, 2H, ArH), 7.38 (d, 3J=9.1 Hz, 2H, ArH), 7.19 (t, 1H, ArH), 7.12 (d, 3J=9.1 Hz, 2H, ArH), 6.98 (d, 3J=9.1 Hz, 2H, ArH)

後処理

  1. temperatureat reflux
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in Et20 (40 mL)
  4. washThe ether solution was washed with 5% aqueous NaOH (3×40 mL) and water (6×40 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customAfter drying in high vacuum overnight
  9. customthe pure product was obtained as a white solid

出典と根拠

ORDレコード
ord-54b763fa48f0470b873aab1b94d435ed
出典データセット
uspto-grants-2013_09
特許番号
US08524194B2

関連ノート

読み込み中…