Boron trifluoride → HCID 58178509, compound

HRID 1625775Notes

Reaction equation

HRID 1625775 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8]([C:10]2[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=2[Cl:17])=O)=[CH:5][CH:4]=1)[CH3:2].C([SiH](CC)CC)C.B(F)(F)F.C(=O)([O-])O.[Na+]>ClCCl.C(#N)C>[Br:16][C:14]1[CH:13]=[CH:12][C:11]([Cl:17])=[C:10]([CH2:8][C:6]2[S:7][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[CH:15]=1

Participants

7

Reactant 4

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 43378853HCID 43378853, compound

Product 1

HCID 58178509HCID 58178509, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the above 5-bromo-2-chlorophenyl 5-ethyl-2-thienyl ketone (5.29 g) in dichloromethane (50 ml)-acetonitrile (50 ml) was cooled under ice-cooling, and thereto were added dropwise triethylsilane (7.69 ml) and boron trifluoride.diethyl ether complex (6.1 ml). Subsequently, the mixture was stirred at room temperature for 3.5 hours, and was cooled again under ice-cooling. To the mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform, washed with brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane) to give 5-bromo-2-chloro-1-(5-ethyl-2-thienylmethyl)benzene (4.52 g) as a colorless liquid.

Workup

  1. temperaturecooling
  2. temperaturewas cooled again under ice-
  3. temperaturecooling
  4. extractionthe mixture was extracted with chloroform
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-c1440076cc9c48659d96f4133cf25a49
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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