Sulfuryl chloride → 4-Chloro-3-(trifluoromethoxy)phenol

HRID 229352Notes

Reaction equation

HRID 229352 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.S(Cl)([Cl:16])(=O)=O>>[Cl:16][C:9]1[CH:8]=[CH:7][C:6]([OH:10])=[CH:5][C:4]=1[O:3][C:2]([F:11])([F:12])[F:1]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 27332613-(Trifluoromethoxy)phenol

Product 1

HCID 177506954-Chloro-3-(trifluoromethoxy)phenol

Procedure

A solution of 3-trifluoromethoxyphenol and sulfuryl chloride is stirred at room temperature until conversion of starting material to product is complete. The excess of sulfuryl chloride is evaporated using a rotary evaporator. The residue is dissolved in dichloromethane and washed with water. The organic layer is separated, dried over MgSO4, filtered and concentrated to yield crude 4-chloro-3-trifluoromethoxyphenol. The crude product is purified over a silica gel column using to give purified product that is used with or without further purification in the following reaction.

Workup

  1. customThe excess of sulfuryl chloride is evaporated
  2. customa rotary evaporator
  3. dissolutionThe residue is dissolved in dichloromethane
  4. washwashed with water
  5. customThe organic layer is separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8df28892e37a4ce3ad6acd462b0ed174
Source dataset
uspto-grants-2009_07
Patent number
US07563792B2

Reaction notes

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