Chloride → HCID 16110536, compound

HRID 1402688Notes

Reaction equation

HRID 1402688 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1.[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16].C(N(C(C)C)CC)(C)C.[Cl-]>ClCCl>[CH3:14][Si:15]([CH3:17])([CH3:16])[C:18]#[C:19][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 66111TrimethylsilylacetyleneHCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 81531Diisopropylethylamine

Product 1

HCID 16110536HCID 16110536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

1 g 5-bromo-1,2,3-trimethoxybenzene, 1.14 mL of trimethylsilylacetylene, 1.4 mL of diisopropylethylamine (DIPEA) and 290 mg of triphenylphosphinpalladium(II) chloride and 39 mg Cu(I)iodide were placed in a dried flask under argon. The mixture was stirred for 1 h at 80° C., after cooling diluted with dichloromethane (DCM) and filtered through a plug of silica. The filtrate was extracted with aqueous ammonia, saturated brine and concentrated. The residue was purified via flash chromatography (SiO2: cyclohexane→cyclohexane/ethylacetate 9:1) to give trimethyl((3,4,5-trimethoxyphenyl)ethynyl)silane.

Workup

  1. temperatureafter cooling
  2. filtrationfiltered through a plug of silica
  3. extractionThe filtrate was extracted with aqueous ammonia, saturated brine
  4. concentrationconcentrated
  5. customThe residue was purified via flash chromatography (SiO2: cyclohexane→cyclohexane/ethylacetate 9:1)

Sources & evidence

ORD record
ord-35d231c0551042e1a4a9d74353ec69c2
Source dataset
uspto-grants-2014_12
Patent number
US08912173B2

Reaction notes

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