Triethylamine → 2-Chloromethyl-1-nitro-4-phenoxy-benzene

HRID 252459ノート

反応式

HRID 252459 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:17]O)([O-:3])=[O:2].C(N(CC)CC)C.CS([Cl:30])(=O)=O>ClCCl>[Cl:30][CH2:17][C:5]1[CH:6]=[C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 574757152-Nitro-5-phenoxy-phenyl-methanol

生成物 1

HCID 574757162-Chloromethyl-1-nitro-4-phenoxy-benzene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a round bottom flask equipped with a nitrogen inlet and a water cooled condenser, 2-nitro-5-phenoxy-phenyl-methanol (2.7 g, 11.1 mmol) and triethylamine (4.7 mL, 33.9 mmol) were dissolved in dichloromethane (100 mL). Methane sulfonyl chloride (2.6 mL, 33.3 mmol) was added to the reaction mixture which was subsequently heated to reflux for 16 h. The next day the reaction was removed from the heating source, allowed to cool and poured into a separatory funnel which contained 1N HCl. The organic phase was washed 2 times with 1N HCl and one time with saturated brine solution. The phases were separated and the ethyl acetate layer was dried with sodium sulfate, filtered and the solvent removed under reduced pressure to yield a residue. The residue was purified by flash chromatography using heptanes:ethyl acetate as the mobile phase (9:1) to yield a residue.

後処理

  1. customTo a round bottom flask equipped with a nitrogen inlet and a water cooled condenser
  2. temperaturewas subsequently heated
  3. temperatureto reflux for 16 h
  4. customThe next day the reaction was removed from the heating source
  5. temperatureto cool
  6. additionpoured into a separatory funnel which
  7. washThe organic phase was washed 2 times with 1N HCl and one time with saturated brine solution
  8. customThe phases were separated
  9. dry with materialthe ethyl acetate layer was dried with sodium sulfate
  10. filtrationfiltered
  11. customthe solvent removed under reduced pressure
  12. customto yield a residue
  13. customThe residue was purified by flash chromatography
  14. customethyl acetate as the mobile phase (9:1) to yield a residue

出典と根拠

ORDレコード
ord-7463ae39f6644496b9b2357afaf8d3ee
出典データセット
uspto-grants-2011_01
特許番号
US07868022B2

反応ノート

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