Dimethyl Sulfide → 5-[4-(4-Trifluoromethylphenoxy)phenoxy]-2,4-hexanedione

HRID 1248092Notes

Reaction equation

HRID 1248092 reaction equation
ClN1C(=O)CCC1=O.CSC.[OH:12][CH:13]([CH:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)[CH3:19])[CH2:14][C:15](=[O:17])[CH3:16].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:35][C:34]([F:36])([F:37])[C:31]1[CH:30]=[CH:29][C:28]([O:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][CH:18]([CH3:19])[C:13](=[O:12])[CH2:14][C:15](=[O:17])[CH3:16])=[CH:22][CH:23]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 202783992-Hexanone, 4-hydroxy-5-[4-[4-(trifluoromethyl)phenoxy]phenoxy]-

Product 1

HCID 202783695-[4-(4-Trifluoromethylphenoxy)phenoxy]-2,4-hexanedione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a stirred solution of N-chlorosuccinimide (0.40 g, 3 mmol) in toluene (10 ml) at -10° under argon is added dimethylsulfide (0.3 ml, 4 mmol). The mixture is cooled to -25°, and 4-hydroxy-5-[4-(4-trifluoromethylphenoxy)phenoxy]-2-hexanone (2 mmol) in several ml of toluene is added dropwise. After 2 hours at -25°, the mixture is cooled to -60°, and a solution of 0.31 g (3 mmol) of triethylamine in several ml of toluene is added dropwise. The reaction mixture is allowed to slowly warm to RT and is quenched by the addition of 5 ml of water. The mixture is poured into ether, and the organic fraction is then separated, washed with 5% HCl, water and brine, and dried over sodium sulfate. Solvent is removed and the residue is purified by prep. TLC to give 5-[4-(4-trifluoromethylphenoxy)phenoxy]-2,4-hexanedione (IX; Z is trifluoromethyl, Y is hydrogen, W is oxygen, R1 is methyl and R2 is methyl).

Workup

  1. temperatureThe mixture is cooled to -25°
  2. temperaturethe mixture is cooled to -60°
  3. customis quenched by the addition of 5 ml of water
  4. additionThe mixture is poured into ether
  5. customthe organic fraction is then separated
  6. washwashed with 5% HCl, water and brine
  7. dry with materialdried over sodium sulfate
  8. customSolvent is removed
  9. customthe residue is purified by prep

Sources & evidence

ORD record
ord-f50dcccbd5ab446e8c1920e6bdcc8821
Source dataset
uspto-grants-1985_06
Patent number
US04522647

Reaction notes

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