Hydrochloric Acid → HCID 12687359, compound

HRID 354593Notes

Reaction equation

HRID 354593 reaction equation
Br[C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:25][Si:26]([C:29]#[CH:30])([CH3:28])[CH3:27].Cl>C(N(CC)CC)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>[CH3:25][Si:26]([C:29]#[C:30][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1)([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66111TrimethylsilylacetyleneHCID 12687356HCID 12687356, compound

Product 1

HCID 12687359HCID 12687359, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

4-(4-Bromophenoxy)benzil (3.81 g, 0.01 mole), trimethylsilylacetylene (1.96 g, 0.02 mole), and dichlorobis(triphenylphosphine)palladium (0.30 g) in triethylamine (20 ml) were placed under a nitrogen atmosphere in a sealed flask and heated at 66°-68° C. for four hours. The cooled brown reaction mixture was poured into cold dilute hydrochloric acid to yield a brown oil which was extracted with methylene chloride. The methylene chloride solution was washed with dilute aqueous hydrochloric acid and water, dried over magnesium sulfate, and concentrated on a rotary evaporator to yield a brown gum (4.0 g). The gum was extracted with boiling cyclohexane (100 ml) (small amount remained insoluble) and the solution treated with charcoal, filtered, and concentrated to yield 4-[(4-[trimethylsilyl)ethynyl]phenoxy]benzil as an orange gum (3.4 g, 85% yield). MS, no M+, major fragment m/e 293 [+CO--C6H4 --O--C6H4 --C≡C--Si(CH3)3 ].

Workup

  1. temperatureheated at 66°-68° C. for four hours
  2. customto yield a brown oil which
  3. extractionwas extracted with methylene chloride
  4. washThe methylene chloride solution was washed with dilute aqueous hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-09173a3b093d41459bc5e59da0308408
Source dataset
uspto-grants-1983_03
Patent number
US04375536

Reaction notes

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