Potassium Carbonate → HCID 66765807, compound

HRID 556773Notes

Reaction equation

HRID 556773 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6][CH:7]=[C:8]([C:9](=O)[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C([SiH](CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6][CH:7]=[C:8]([CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 23154554HCID 23154554, compound

Product 1

HCID 66765807HCID 66765807, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a mixture of 1-(5-bromobenzo[b]thiophen-3-yl)-2-phenylethanone (1.1 g) and triethylsilane (1.5 g) was added trifluoro acetic acid (10 mL) at room temperature, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into an ice-cooled saturated potassium carbonate aqueous solution, and the mixture was extracted with diethyl ether. The organic layer washed with water and brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane) to give the title compound (0.94 g).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane)

Sources & evidence

ORD record
ord-65d80e0f8c8443269546211a9f251803
Source dataset
uspto-grants-2011_11
Patent number
US08058245B2

Reaction notes

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