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

HRID 853926Notes

Reaction equation

HRID 853926 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-349c29154c9e4840b215a337519f9022
Source dataset
uspto-grants-2007_08
Patent number
US07256218B2

Reaction notes

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