Dichloroacetyl chloride → HCID 57085216, compound

HRID 2164576Notes

Reaction equation

HRID 2164576 reaction equation
[Si:1]([O:8][CH:9]=[C:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:22][CH:23]([Cl:27])[C:24](Cl)=[O:25]>C1CCCCC1.C(Cl)Cl>[Si:1]([O:8][CH:9]=[C:10]1[CH:11]2[CH:12]([C:23]([Cl:27])([Cl:22])[C:24]2=[O:25])[CH:13]=[CH:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 13476948HCID 13476948, compound

Product 1

HCID 57085216HCID 57085216, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

A 3-neck, 5 L flask equipped with a heating mantle, a mechanical stirrer, an argon inlet, and a pressure-equalized dropping funnel was charged with the 6-(tert-butyldimethylsilyloxy)fulvene from the previous Preparation dissolved in 2 L of cyclohexane. After this solution was brought to reflux, 150 mL of triethylamine was added in one portion. Then, 100 mL of dichloroacetyl chloride was added dropwise to the refluxing mixture over a 1.5 hr period. The cooled reaction mixture was diluted with 1.5 L of methylene chloride and filtered to remove the triethylamine hydrochloride by-product. The dark solution of the crude reaction product could be stored as such for a few days. The solvent was removed by evaporation immediately before its use in the next reaction.

Workup

  1. customA 3-neck, 5 L flask equipped with a heating mantle, a mechanical stirrer, an argon inlet
  2. temperatureto reflux
  3. customThe cooled reaction mixture
  4. filtrationfiltered
  5. customto remove the triethylamine hydrochloride by-product
  6. customThe dark solution of the crude reaction product
  7. customsuch for a few days
  8. customThe solvent was removed by evaporation immediately before its use in the next reaction

Sources & evidence

ORD record
ord-6215b059dbd240c088e20b5d9fd63cb0
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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