Trimethylsilylacetylene → HCID 71237756, compound

HRID 1496842Notes

Reaction equation

HRID 1496842 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:11])[C:5]([O:9][CH3:10])=[C:6]([F:8])[CH:7]=1.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13].C(N(C(C)C)CC)(C)C>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[F:8][C:6]1[CH:7]=[C:2]([C:13]#[C:12][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=[C:4]([F:11])[C:5]=1[O:9][CH3:10]

Participants

7

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 27732874-Bromo-2,6-difluoroanisole

Product 1

HCID 71237756HCID 71237756, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2 g 5-bromo-1,3-difluoro-2-methoxy-benzene, 1.76 g ethynyl-trimethyl-silane, 629 mg bis(triphenylphosphine)palladium(II) dichloride, 3.1 ml diisopropylethylamine, and 85 mg copper iodide in 20 ml acetonitrile was degassed then heated at 80° C. for 2 hours. The mixture was diluted with dichloromethane and filtered through a plug of silica, washed with dilute ammonia and brine then dried over sodium sulphate, filtered and concentrated in vacuo. Purification over silica afforded 1.71 g (3,5-difluoro-4-methoxy-phenylethynyl)-trimethyl-silane.

Workup

  1. customwas degassed
  2. additionThe mixture was diluted with dichloromethane
  3. filtrationfiltered through a plug of silica
  4. washwashed with dilute ammonia and brine
  5. dry with materialthen dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification over silica

Sources & evidence

ORD record
ord-473124cf420a407cac00792bd3e1a5f8
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

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