Dichloromethane → HCID 16638363, compound

HRID 1987485Notes

Reaction equation

HRID 1987485 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[Al+3].[Cl-].[Cl-].[Cl-].C(Cl)Cl.[CH3:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1>O>[CH3:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][C:25]=1[C:5]([C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[S:2][CH3:1])=[O:6]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7809P-XyleneHCID 6451240Aluminum(III) ChlorideHCID 125767982-(Methylsulfanyl)benzoyl chloride

Product 1

HCID 16638363HCID 16638363, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.2 g 2-(methylthio)benzoyl chloride (B) and 1.55 g AlCl3 at 0° C. was added slowly 20 ml DCM. The mixture was stirred 5 minutes at ambient temperature before 7.8 g p-xylene was added slowly. The reaction was stirred 30 minutes at ambient temperature before water was added slowly. The mixture was extracted with DCM (2×50 ml). The combined organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. Flash silica chromatography (hexane:ethyl acetate 85:15) afforded 0.758 g product.

Workup

  1. additionwas added slowly
  2. additionwas added slowly
  3. extractionThe mixture was extracted with DCM (2×50 ml)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-612f1d95ec86450da77a2dd92654887e
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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