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

HRID 393911

반응식

HRID 393911 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2cbb3bcbb91f4deead7c783c0e3e4ff3
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809206B2

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