2-Chloro-4-Phenylphenol → 3-Chlorobiphenyl-4-yl trifluoromethanesulfonate

HRID 735060Notes

Reaction equation

HRID 735060 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Cl:16][C:17]1[CH:18]=[C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:21][C:22]=1O.C(N(CC)CC)C>ClCCl>[Cl:16][C:17]1[CH:18]=[C:19]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:20]=[CH:21][C:22]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 70742-Chloro-4-PhenylphenolHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 180010793-Chlorobiphenyl-4-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6.7 mL (40.32 mmol) of trifluoromethanesulfonic acid anhydride dissolved in 5 mL dichloromethane is added dropwise between −10° C. to −5° C. to a solution of 7.5 g (36.65 mmol) of 3-chlorobiphenyl-4-ol and 6.1 mL (44 mmol) of triethylamine in 100 mL of dichloromethane. Then the mixture is stirred for 30 minutes. The reaction solution is then extracted with water, the organic phase is separated off and filtered through an Alox frit. The filtrate is concentrated by evaporation. Yield: 12 g (97% of theory); C13H8ClF3O3S (M=336.72); calc.: molecular ion peak (M+H)+: 336/338 (Cl); found: molecular ion peak (M+H)+: 336/338 (Cl); Rf value: 0.7 (silica gel, petroleum ether/ethyl acetate (5:1)).

Workup

  1. extractionThe reaction solution is then extracted with water
  2. customthe organic phase is separated off
  3. filtrationfiltered through an Alox frit
  4. concentrationThe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-882d8d722cab415289205b64abc29f4d
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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