Water → 2,6-Dimethyl-4-nitrophenyl trifluoromethanesulfonate

HRID 392883Notes

Reaction equation

HRID 392883 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](O)=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1C.N1C=CC=C[CH:14]=1.[F:19][C:20]([F:33])([F:32])[S:21]([O:24]S(C(F)(F)F)(=O)=O)(=[O:23])=[O:22].O>ClCCl>[F:19][C:20]([F:33])([F:32])[S:21]([O:24][C:7]1[C:6]([CH3:14])=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=1[CH3:1])(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 135714543,4-Dimethyl-2-nitrophenol

Product 1

HCID 226621252,6-Dimethyl-4-nitrophenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 150 g (0.9 mol) of dimethylnitrophenol in 700 ml of dichloromethane is cooled to −15° C. 181 ml of pyridine are added. 308.8 g (1.09 mol) of trifluoromethanesulphonic anhydride are then metered in dropwise over a period of 2 h in such a way that the reaction temperature does not exceed −5° C. Then, at a temperature of −5° C., 150 ml of water are added. The organic phase is extracted successively with HCl (1 molar, about 300 ml) and water (twice), each at 3-5° C. The solvent is removed in vacuo, and the residue is stirred with petroleum ether. The precipitate is filtered off with suction. A further fraction is obtained by cooling the mother liquor. Yield: 232 g (85%)

Workup

  1. customof 2 h
  2. customdoes not exceed −5° C
  3. extractionThe organic phase is extracted successively with HCl (1 molar, about 300 ml) and water (twice), each at 3-5° C
  4. customThe solvent is removed in vacuo
  5. filtrationThe precipitate is filtered off with suction
  6. customA further fraction is obtained
  7. temperatureby cooling the mother liquor

Sources & evidence

ORD record
ord-517e215f732a4599a0491def536914c2
Source dataset
uspto-grants-2004_10
Patent number
US06803480B2

Reaction notes

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