Carbon Tetrachloride → HCID 67171120, compound

HRID 1475785Notes

Reaction equation

HRID 1475785 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([Si](CC)(CC)CC)[C:8]2[O:9][C:10]([F:13])([F:12])[O:11][C:7]=2[CH:6]=1)=[O:4].C(Cl)(Cl)(Cl)Cl.[I:28]Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([I:28])[C:8]2[O:9][C:10]([F:13])([F:12])[O:11][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 24640Iodine chloride2×HCID 67170643HCID 67170643, compound

Product 1

HCID 67171120HCID 67171120, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
77 °C

Procedure

17.0 g of 2,2-difluoro-7-triethylsilanyl-benzo[1,3]dioxole-5-carboxylic acid methyl ester were dissolved using 100 ml of CCl4 and 2.9 ml of ICl added. The mixture was then stirred for 3 h at 77° C., 1.5 ml of ICl added and stirred for 2 h at 77° C. The mixture was then allowed to cool to room temperature, 200 ml of CH2Cl2 added, and washed three times using 300 ml of a saturated aqueous Na2SO3-solution each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:20 yielded 10.2 g of the title compound, colorless oil. Rf (EA/HEP 1:20)=0.30

Workup

  1. additionadded
  2. stirringstirred for 2 h at 77° C
  3. temperatureto cool to room temperature
  4. washwashed three times
  5. customThe organic layer was then dried
  6. customevaporated

Sources & evidence

ORD record
ord-2eb38d465131412896d18c950ab19579
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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