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

HRID 393910Notes

Reaction equation

HRID 393910 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[N+:23]([C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(N(CC)CC)C>CN(C=O)C.ClCCl>[N+:1]([C:4]1[CH:12]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][C:29]1[CH:30]=[CH:31][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=1)=[O:7])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 184292Benzoic acid, 4-(methylsulfonyl)-2-nitro-

Product 1

HCID 226483334-Nitrophenyl 2-nitro-4-(methylsulfonyl)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A 100-mL 2-necked round bottom flask was fitted with thermometer, magnetic stirrer, and reflux condenser with nitrogen bypass. The flask was charged with 1.23 g (5 mmol) of 2-nitro-4-(methylsulfonyl)benzoic acid, 2 drops of DMF, and 20 mL of dichloromethane. Oxalyl chloride (0.70 g, 5.5 mmol) was added dropwise and the mixture was stirred for 1 hr. A solution consisting of 0.70 g (5 mmol) of 4-nitrophenol, 0.55 g (5.5 mmol) of triethylamine and 5 mL of dichloromethane was added and the mixture was stirred for 1 hr. The mixture was diluted with 100 mL of dichloromethane, washed twice with 100 mL portions of aqueous sodium bicarbonate, once with 100 mL of water, dried with magnesium sulfate, filtered, and volatiles removed under reduced pressure to give the title product as 1.56 g of off-white solid, m.p. 171-173° C. 1H NMR (CDCl3): δ 3.19 (s, 3), 7.47 (m, 2), 8.10 (m, 1), 8.38 (m, 3), 8.69 (m, 1).

Workup

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

Sources & evidence

ORD record
ord-e549951fc57b4f08b4567267d290dd2b
Source dataset
uspto-grants-2004_10
Patent number
US06809206B2

Reaction notes

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