Chlorodifluoromethane → 4-Chloro-4'-difluoromethylthiomethyl-benzophenone

HRID 2098

Reaction equation

HRID 2098 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][SH:15])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].O1CCOCC1.[F:26][CH:27](Cl)[F:28]>O>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15][CH:27]([F:28])[F:26])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6372ChlorodifluoromethaneHCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 196893804-Chloro-4'-mercaptomethylbenzophenone2×

Product 1

HCID 196893694-Chloro-4'-difluoromethylthiomethyl-benzophenoneYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-chloro-4'-mercaptomethylbenzophenone (14.7 g) and potassium hydroxide (15 g) was added to a solvent comprising dioxane (100 ml) and water (100 ml). Difluoromethyl chloride was blown into this solution at 60° C. until the starting material 4-chloro-4'-mercaptomethylbenzophenone disappeared. The reaction product was cooled to room temperature and then subjected to filtration. The organic layer as the filtrate was dried over anhydrous magnesium sulfate add concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the desired product (6.4 g, melting point: 34° to 35° C., yield: 36%).

Workup

  1. filtrationsubjected to filtration
  2. dry with materialThe organic layer as the filtrate was dried over anhydrous magnesium sulfate
  3. additionadd
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-54662bdd64d74fb6bcb38cb65a7a5fc0
Source dataset
uspto-grants-1998_03
Patent number
US05728699

Linked notes

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