2,3-Dichlorobenzene-1-sulfonyl chloride → 3-(2,3-Dichlorophenylsulfonyloxy)-5-methylphenol

HRID 368529

Reaktionsgleichung

Reaktionsgleichung von HRID 368529
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[S:19](Cl)(=[O:21])=[O:20]>C([O-])(O)=O.[Na+].C(OCC)C>[OH:5][C:4]1[CH:3]=[C:2]([O:10][S:19]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=2[Cl:11])(=[O:21])=[O:20])[CH:9]=[C:7]([CH3:8])[CH:6]=1

Komponenten

5

Edukt 2

HCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Produkt 1

HCID 109037243-(2,3-Dichlorophenylsulfonyloxy)-5-methylphenolAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of orcinol monohydrate (0.71 g, 5.0 mmol) and 2,3-dichlorobenzenesulfonyl chloride (1.23 g, 5.0 mmol) in saturated NaHCO3 (20 mL) and diethyl ether (20 mL was stirred at room temperature for 2 days. The reaction mixture was quenched with water (50 mL) and extracted with ethyl acetate (3×50 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (methylene chloride to 2% ethyl acetate in methylene chloride) to give the title compound as a pale yellow oil (0.89 g, 55%). 1H-NMR (300 MHz, CDCl3) δ 2.24 (s, 3 H), 5.23 (s, 1 H), 6.43 (t, 1 H, J=2.2 Hz), 6.54 (d, 2 H, J=1.1 Hz), 7.34 (t, 1 H, J=8.1 Hz), 7.75 (dd, 1 H, J=0.8, 4.0 Hz), and 7.91 (dd, 1 H, J=0.8, 4.0 Hz).

Aufarbeitung

  1. customThe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe organic phase was washed with brine (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography (methylene chloride to 2% ethyl acetate in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-467dae723123476bbe2e542fa2e81eb6
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133315

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