2-Trifluoromethylbenzenesulphonyl chloride → 5-Methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenol

HRID 442894Notes

Reaction equation

HRID 442894 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[F:11][C:12]([F:24])([F:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20]>C([O-])(O)=O.[Na+].C(OCC)C.O>[CH3:8][C:7]1[CH:9]=[C:2]([O:10][S:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([F:11])([F:23])[F:24])(=[O:21])=[O:20])[CH:3]=[C:4]([OH:5])[CH:6]=1

Participants

6

Reactant 2

HCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 227226495-Methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenolYield 55%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Orcinol monohydrate (2.84 g, 20.0 mmol) and 2-trifluoromethylbenzenesulfonyl chloride (4.90 g, 20.0 mmol) were mixed in saturated aqueous NaHCO3 (70 mL) and diethyl ether (70 mL). The biphasic mixture was stirred vigorously at room temperature overnight. The reaction mixture was diluted with water (100 mL) and extracted into ethyl acetate (3×80 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane) to give the title compound as a white solid (3.65 g, 55%). 1H-NMR (300 MHz, CDCl3) δ 8.12 (d, J=8.0 Hz, 1 H), 7.98 (d, J=7.9 Hz, 1 H), 7.80 (t, J=8.2 Hz, 1 H), 7.69 (t, J=7.8 Hz, 1 H), 6.55 (s, 1 H), 6.48 (s, 1 H), 6.39 (s, 1 H), 5.11 (s, 1 H), 2.23 (s, 3 H).

Workup

  1. extractionextracted into ethyl acetate (3×80 mL)
  2. washThe organic phase was washed with brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent in vacuo
  5. customthe residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-86fabd4499e24b38aeff0345b47b251f
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

Loading…