2-Chloro-6-methylphenol → HCID 18700110, compound

HRID 2289323Notes

Reaction equation

HRID 2289323 reaction equation
[OH:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].FC(S(OO[CH2:19][C:20]([F:23])([F:22])[F:21])(=O)=O)(F)F.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:21][C:20]([F:23])([F:22])[CH2:19][O:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 68982-Chloro-6-methylphenolHCID 10796Cesium carbonateHCID 187000722,2,2-Trifluoroethoxy trifluoromethylsulfonate

Product 1

HCID 18700110HCID 18700110, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-hydroxy-3-chlorotoluene (5 g, 35 mmol) in DMF (75 mL) at 0° C. was added 2,2,2-trifluoroethoxy trifluoromethylsulfonate (16 g, 70 mmol) and Cs2CO3 (22 g, 68 mmol). The mixture was stirred at 0° C. for 3 h and then at ambient temperature for 14 h. The solvent was removed under reduced pressure. The residue was partitioned between EtOAc (150 mL) and water (3×75 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 1:4 EtOAc:hexanes as eluant to give 2-(2,2,2-trifluoroethoxy)-3-chlorotoluene as an oil.

Workup

  1. waitat ambient temperature for 14 h
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was partitioned between EtOAc (150 mL) and water (3×75 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-72e3c4ef864f4d419922ec2d6ad3a37d
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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