Water → HCID 54099074, compound

HRID 1421544Notes

Reaction equation

HRID 1421544 reaction equation
C(#N)C.Br[CH2:5][C:6]1[CH:20]=[CH:19][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1.[CH3:21][SH:22].[Na].O>C1(C)C=CC=CC=1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]([C:9]2[CH:19]=[CH:20][C:6]([CH2:5][S:22][CH3:21])=[CH:7][CH:8]=2)=[O:11])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 45051789Methylmercaptan sodium

Product 1

HCID 54099074HCID 54099074, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To an acetonitrile solution (200 ml) of 4-bromomethyl-4'-fluorobenzophenone (20 g), an aqueous 15% sodium methylmercaptan solution (60 ml) was added and the mixture was heated for 6 hours with refluxing. After the reaction mixture was restored to room temperature, water (500 ml) and toluene (300 ml) were added. The organic layer was separated, which was then successively washed with an aqueous 2N sodium hydroxide solution and water, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the crude product was purified by silica gel column chromatography (developing solvent n-hexane:ethyl acetate=9:1) to obtain 4-fluoro-4'-methylmercaptomethylbenzophenone (17 g).

Workup

  1. temperaturethe mixture was heated for 6 hours
  2. temperaturewith refluxing
  3. customwas restored to room temperature
  4. customThe organic layer was separated
  5. washwhich was then successively washed with an aqueous 2N sodium hydroxide solution and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter distilling off the solvent
  8. customthe crude product was purified by silica gel column chromatography (developing solvent n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-4018569a4e19487a83b725104fac9035
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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