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Sodium Carbonate → Methyl 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-3-methoxythiophene-2-carboxylate

HRID 450499
ノート
印刷プレビュー

反応式

HRID 450499 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:18]1[C:19]([O:35][CH3:36])=[C:20]([C:31]([O:33][CH3:34])=[O:32])[S:21][C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[C:19]([O:35][CH3:36])=[C:20]([C:31]([O:33][CH3:34])=[O:32])[S:21][C:22]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 67502528Methyl 4-bromo-5-(2,4-dichlorophenyl)-3-methoxythio-phene-2-carboxylate

生成物 1

HCID 67495513Methyl 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-3-methoxythiophene-2-carboxylate収率 75.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

7.75 g of (4-chlorophenyl)boronic acid and then, dropwise, 40.93 ml of a 2M solution of Na2CO3 are added to a solution of 16.21 g of the compound of step B) in 110 ml of toluene. Argon is sparged into the reaction mixture for 30 minutes, then 2.36 g of Tetrakis are added and heating is carried out at 110° C. for 18 hours. After cooling to AT, the reaction mixture is rinsed with 80 ml of distilled water, then extraction is carried out with 80 ml of EtOAc, drying is carried out over Na2SO4, and the solvent is evaporated off under vacuum. The reaction crude is purified by silica gel chromatography, elution being carried out with heptane and then with a heptane/EtOAc mixture (85/15; v/v). 13.23 g of the expected compound are obtained.

後処理

  1. customArgon is sparged into the reaction mixture for 30 minutes
  2. addition2.36 g of Tetrakis are added
  3. temperatureheating
  4. temperatureAfter cooling to AT
  5. washthe reaction mixture is rinsed with 80 ml of distilled water
  6. extractionextraction
  7. customdrying
  8. customthe solvent is evaporated off under vacuum
  9. customThe reaction crude
  10. customis purified by silica gel chromatography, elution

出典と根拠

ORDレコード
ord-16b580ed79724cb39d1800511ed3c0e2
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08486971B2

反応ノート

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