Chloroform → HCID 23145779, compound

HRID 13348

Reaction equation

HRID 13348 reaction equation
C(Cl)(Cl)Cl.[N+:5]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([F:16])[CH:9]=1)([O-:7])=[O:6].[CH2:17]([Si](C)(C)C)[CH:18]=[CH2:19]>C(OCC)(=O)C.[Ti](Cl)(Cl)(Cl)Cl>[F:16][C:10]1[CH:9]=[C:8]([N+:5]([O-:7])=[O:6])[CH:15]=[CH:14][C:11]=1[CH:12]([OH:13])[CH2:19][CH:18]=[CH2:17]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 69808AllyltrimethylsilaneHCID 45629192-Fluoro-4-nitrobenzaldehyde

Product 1

HCID 23145779HCID 23145779, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

0.65 ml of titanium tetrachloride was added to a chloroform (12 ml) solution of 2.00 g of 4-nitro-2-fluoro-benzaldehyde produced according to the method described in U.S. Pat. No. 6,239,152, and the reaction liquid was stirred at room temperature for 10 minutes, and then 2.4 ml of allyl-trimethyl-silane was added to it, and the reaction liquid was stirred at room temperature for 20 minutes. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1) to obtain the entitled compound as an orange solid.

Workup

  1. customproduced
  2. custom6,239,152, and the reaction liquid
  3. customthe reaction liquid
  4. stirringwas stirred at room temperature for 20 minutes
  5. customThe reaction liquid
  6. washwashed with water and saturated saline
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe solvent was evaporated away under reduced pressure
  9. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-e409d2c505314342bc35b68cf061a516
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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