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Ethylenediaminetetraacetic Acid → Carbonylbis[3-(2-pyridyl)benzene]

HRID 2117821
ノート
印刷プレビュー

反応式

HRID 2117821 の反応式
[C:1]([Li])([CH3:4])([CH3:3])C.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.Br[C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=1)[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21](Br)[CH:20]=1)=[O:18].[CH2:29](N(CC(O)=O)CC(O)=O)[CH2:30][N:31](CC(O)=O)CC(O)=O>[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCCC1.CCCCC>[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:4]2[CH:1]=[CH:3][CH:29]=[CH:30][N:31]=2)[CH:20]=1)([C:16]1[CH:26]=[CH:27][CH:28]=[C:14]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:15]=1)=[O:18]
参加物反応条件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 6049Ethylenediaminetetraacetic AcidHCID 79732-BromopyridineHCID 12731928Bis(3-bromophenyl)methanoneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 23135812Carbonylbis[3-(2-pyridyl)benzene]収率 75.8%

試薬・触媒・溶媒 4

HCID 3007855
Zincchloride
触媒
HCID 178418397HCID 178418397、化合物触媒
HCID 8003Pentane溶媒
HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-70 °C

実験手順

In a nitrogen atmosphere, a n-pentane solution of t-butyllithium (17.8 ml, 1.60M, 28.5 mmol) was dropwise added to tetrahydrofuran cooled to −70° C., then a tetrahydrofuran (5 ml) solution of 2-bromopyridine (1.2 ml, 12.9 mmol) was added thereto while 15 minutes, after a dropwise, the mixture was stirred at −70° C. for 30 minutes. Then, a tetrahydrofuran solution of zinc chloride (31.8 ml, 0.50 M, 15.9 mmol) was added to the mixture while 10 minutes. Thereafter, the temperature of the reaction mixture was allowed to warm to room temperature while 1 hour, tetrakis(triphenylphosphine)palladium (203 mg) and 3,3′-dibromobenzophenone (2.0 g, 5.88 mmol) were successively added thereto, the reaction mixture was stirred under reflux for 18 hours. After the reaction mixture was allowed to cool, then the mixture was poured into a mixture of ethylenediaminetetraacetic acid (7.0 g)/an aqueous saturated sodium hydrogen carbonate solution (210 ml), an organic layer was separated, furthermore an aqueous layer was extracted with toluene. The organic layer was combined, and the solvent was distilled off, and the residue was purified by silica gel column chromatography and recrystallization, thereby obtaining 1.5 g of carbonylbis[3-(2-pyridyl)benzene as white powder. Yield: 75.8%.

後処理

  1. temperatureto warm to room temperature while 1 hour
  2. stirringthe reaction mixture was stirred
  3. temperatureunder reflux for 18 hours
  4. temperatureto cool
  5. customan organic layer was separated
  6. extractionfurthermore an aqueous layer was extracted with toluene
  7. distillationthe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography and recrystallization

出典と根拠

ORDレコード
ord-617ddd39ded6445d8b1148585546c17e
出典データセット
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07442797B2

反応ノート

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