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Pyridine → dimethyl 5-phenylethynylisophthalate

HRID 1925198
ノート
印刷プレビュー

反応式

HRID 1925198 の反応式
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.N1C=CC=CC=1>[Cu](I)I.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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:18]1([C:17]#[C:16][C:2]2[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 1049PyridineHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester

生成物 1

HCID 10946313dimethyl 5-phenylethynylisophthalate収率 75%

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 962Water溶媒

実験手順

In a 1 L four-neck flask equipped with a thermometer, a Dimroth condenser, a nitrogen introduction tube and an agitator, 99.7 g (0.365 mol) of the second intermediate (dimethyl 5-bromoisophthalate), 1.1 g (0.00419 mol) of triphenylphosphine, 0.275 g (0.00144 mol) of copper iodide and 41.0 g (0.401 mol) of phenylacethylene were charged and nitrogen was passed into the flask. Then, 375 mL of dehydrated triethylamine and 200 mL of dehydrated pyridine were added therein and the mixture was agitated and dissolved. After passing the nitrogen for one hour, 0.3 g (0.000427 mol) of dichlorobis(triphenyl phosphine)palladium was quickly added and the mixture was heated and refluxed in an oil bath for one hour. Then, triethylamine and pyridine were removed under reduced pressure to obtain a brown viscous solution. The solution was added to 500 mL of water and filtered to separate a solid. The solid was washed with 500 mL of water, 500 mL of 5 mol/L hydrochloric acid and 500 mL of water each two times and dried under reduced pressure at 50° C. Thus, 80.6 g of dimethyl 5-phenylethynylisophthalate was obtained (the yield was 75%).

後処理

  1. customIn a 1 L four-neck flask equipped with a thermometer
  2. dissolutiondissolved
  3. customfor one hour
  4. temperaturethe mixture was heated
  5. temperaturerefluxed in an oil bath for one hour
  6. customThen, triethylamine and pyridine were removed under reduced pressure
  7. customto obtain a brown viscous solution
  8. filtrationfiltered
  9. customto separate a solid
  10. washThe solid was washed with 500 mL of water, 500 mL of 5 mol/L hydrochloric acid and 500 mL of water each two times
  11. customdried under reduced pressure at 50° C

出典と根拠

ORDレコード
ord-09351e3426844c1fb89aae7e82fa4405
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178631B2

反応ノート

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