Chlorosuccinimide → HCID 68108720, compound

HRID 385152Notes

Reaction equation

HRID 385152 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][C:13]([F:16])([F:15])[F:14].[Cl:17]N1C(=O)CCC1=O.FC(F)(F)S(O)(=O)=O>C(Cl)(Cl)Cl.CO>[Cl:17][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([O:12][C:13]([F:14])([F:15])[F:16])[C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 3

HCID 31398ChlorosuccinimideHCID 62406Trifluoromethanesulfonic acidHCID 68107964HCID 68107964, compound

Product 1

HCID 68108720HCID 68108720, compoundYield 112.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 4-hydroxy-3-trifluoromethoxybenzoate (2.05 g) was dissolved in chloroform (20 mL) and methanol (3 mL), and N-chlorosuccinimide (1.39 g) and trifluoromethanesulfonic acid (0.05 mL) were added to the solution, and then the mixture was stirred at 50° C. for 19 hours. The solvent was distilled off under reduced pressure and 1N hydrochloric acid was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (2.64 g) as a yellow solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and 1N hydrochloric acid
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a4f00af8520148b4b9d6b8aa00e52d36
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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