Sodium Carbonate → Methyl 4-bromo-5-(2,4-dichlorophenyl)-3-methoxythio-phene-2-carboxylate

HRID 450498ノート

反応式

HRID 450498 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].[Br:18][C:19]1[C:20]([O:29][CH3:30])=[C:21]([C:25]([O:27][CH3:28])=[O:26])[S:22][C:23]=1Br>C1(C)C=CC=CC=1>[Br:18][C:19]1[C:20]([O:29][CH3:30])=[C:21]([C:25]([O:27][CH3:28])=[O:26])[S:22][C:23]=1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 2808414Methyl 4,5-dibromo-3-methoxythiophene-2-carboxylate

生成物 1

HCID 67502528Methyl 4-bromo-5-(2,4-dichlorophenyl)-3-methoxythio-phene-2-carboxylate収率 47.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

16.60 g of (2,4-dichlorophenyl)boronic acid and then, dropwise, 87 ml of a 2M solution of Na2CO3 are added to a solution of 28.70 g of the compound of step A) in 110 ml of toluene. Argon is sparged into the reaction mixture for 30 minutes, 5.03 g of tetrakis are then added and the mixture is heated at 110° C. for 18 hours. After cooling to AT, 80 ml of distilled water are added to the reaction mixture, 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). 16.21 g of the expected compound are obtained.

後処理

  1. customArgon is sparged into the reaction mixture for 30 minutes
  2. addition5.03 g of tetrakis are then added
  3. temperatureAfter cooling to AT, 80 ml of distilled water
  4. additionare added to the reaction mixture, extraction
  5. customdrying
  6. customthe solvent is evaporated off under vacuum
  7. customThe reaction crude
  8. customis purified by silica gel chromatography, elution

出典と根拠

ORDレコード
ord-ba9c01f3100049a6899c8726b0ce7e2d
出典データセット
uspto-grants-2013_07
特許番号
US08486971B2

反応ノート

読み込み中…