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

HRID 1977976Notes

Reaction equation

HRID 1977976 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>[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

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 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 NaHCO3 (70 mL) and diethyl ether (70 mL). The biphasic mixture was stirred vigorously at room temperature overnight. The reaction mixture was quenched 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) δ8.12 (d, J=8.0 Hz, 1H), 7.98 (d, J=7.9 Hz, 1H), 7.80 (t, J=8.2 Hz, 1H), 7.69 (t, J=7.8 Hz, 1H), 6.55 (s, 1H), 6.48 (s, 1H), 6.39 (s, 1H), 5.11 (s, 1H), 2.23 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted into ethyl acetate (3×80 mL)
  3. washThe organic phase was washed with brine (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent in vacuo
  6. customthe residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-1f57e252e50f4e89bbb82ac9ad6b7cb0
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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