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Phenylacetylene → Thiophene, 2-(phenylethynyl)-

HRID 274423
ノート
印刷プレビュー

反応式

HRID 274423 の反応式
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[C:7]1([C:13]#[CH:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>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.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:14]#[C:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 10821PhenylacetyleneHCID 138512-Bromothiophene

生成物 1

HCID 1238176Thiophene, 2-(phenylethynyl)-収率 57.6%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物
触媒
HCID 8471Triethylamine溶媒

実験手順

1 g (0.00142 mol) of bis-(triphenylphosphine)palladium chloride, 5 g (0.0262 mol) of copper iodide and 8.5 g (0.0324 mol) of triphenylphosphine were added in succesion to a solution of 163 g (1 mol) of 2-bromothiophene and 127.5 g (1.25 mol) of phenylacetylene in 850 ml of triethylamine at 25° C. Stirring was carried out for twelve hours under a nitrogen atmosphere at 80° C., after which the mixture was filtered and the filtrate was evaporated down under reduced pressure. 600 ml of methylene chloride were added to the residue and the solution was washed with three times 200 ml of water, dried over Na2SO4 and evaporated down under reduced pressure, after which 200 ml of n-pentane were added. The crystals thus obtained were filtered off under suction and dried. 106 g (57.6% of theory) of 1-(2-thienyl)-2-phenylacetylene were obtained as pale yellow crystals of melting point 49°-59 ° C. (Active Ingredient Example 1.001).

後処理

  1. waitwas carried out for twelve hours under a nitrogen atmosphere at 80° C.
  2. filtrationafter which the mixture was filtered
  3. customthe filtrate was evaporated down under reduced pressure
  4. addition600 ml of methylene chloride were added to the residue
  5. washthe solution was washed with three times 200 ml of water
  6. dry with materialdried over Na2SO4
  7. customevaporated down under reduced pressure
  8. additionafter which 200 ml of n-pentane were added
  9. customThe crystals thus obtained
  10. filtrationwere filtered off under suction
  11. customdried

出典と根拠

ORDレコード
ord-69351cee38124d8aae27462d77cabe0b
出典データセット
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05389656

反応ノート

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