4-Nitrophenol → 4-Nitrophenyl 2-chloro-4-(methylsulfonyl)benzoate

HRID 393911

反応式

HRID 393911 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(Cl)(=O)C(Cl)=O.[N+:21]([C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1)([O-:23])=[O:22].C(N(CC)CC)C>CN(C=O)C.ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:27]1[CH:28]=[CH:29][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=1)=[O:5]

参加物

7

反応物 4

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7358632-Chloro-4-(methylsulfonyl)benzoic acid

生成物 1

HCID 226483244-Nitrophenyl 2-chloro-4-(methylsulfonyl)benzoate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒3 回

実験手順

A 200-mL round bottom flask was fitted with thermometer, magnetic stirrer, and reflux condenser with nitrogen bypass. The flask was charged with 0.94 g (4 mmol) of 2-chloro-4-(methylsulfonyl)benzoic acid, 2 drops of DMF, and 20 mL of dichloromethane. Oxalyl chloride (0.56 g, 4.4 mmol) was added dropwise and the mixture was stirred for 1 hr. A solution consisting of 0.62 g (4 mmol) of 4-nitrophenol, 0.44 g (4.4 mmol) of triethylamine and 5 mL of dichloromethane was added slowly. The mixture was stirred for 1 hr, diluted with 100 mL of dichloromethane, washed twice with 100 mL portions of dilute aqueous sodium bicarbonate, once with water, dried over magnesium sulfate, filtered, and volatiles removed under reduced pressure to give the title product as 1.30 g of off-white solid, m.p. 123-125° C. 1H NMR (CDCl3): δ 3.14 (s, 3), 7.48 (m, 2), 8.00 (m, 1), 8.14 (m, 1), 8.21 (m, 1), 8.36 (m, 2).

後処理

  1. customA 200-mL round bottom flask was fitted with thermometer, magnetic stirrer
  2. temperaturereflux condenser with nitrogen bypass
  3. additionwas added slowly
  4. stirringThe mixture was stirred for 1 hr
  5. washwashed twice with 100 mL portions of dilute aqueous sodium bicarbonate, once with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customvolatiles removed under reduced pressure

出典と根拠

ORDレコード
ord-2cbb3bcbb91f4deead7c783c0e3e4ff3
出典データセット
uspto-grants-2004_10
特許番号
US06809206B2

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