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

HRID 450498노트

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HRID 450498 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ba9c01f3100049a6899c8726b0ce7e2d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486971B2

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