Chloroform → HCID 67973500, 화합물

HRID 708308

반응식

HRID 708308 반응식
Br[C:2]1[S:3][C:4](Br)=[CH:5][C:6]=1[Br:7].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[C:20](=[O:23])([O-])[O-].[Na+].[Na+].C(Cl)(Cl)Cl>C1COCC1.O.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.CCOC(C)=O>[Br:7][C:6]1[CH:5]=[C:4]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[S:3][C:2]=1[C:11]1[CH:16]=[CH:15][C:14]([O:23][CH3:20])=[CH:13][CH:12]=1

참가 물질

8

반응물 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 76592Thiophene, 2,3,5-tribromo-HCID 201262(4-Methoxyphenyl)boronic acid

생성물 1

HCID 67973500HCID 67973500, 화합물수율 65%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

2,3,5-Tribromothiophene (6.42 g, 20 mmol), 4-methoxyphenylboronic acid (6.38 g, 42 mmol) and sodium carbonate (8.5 g, 80 mmol) were stirred in THF/water mixture (125/50 ml) for 90 min at RT under argon flushing. Pd(PPh3)4 (693 mg, 0.6 mmol) was added. The mixture was refluxed for 16 h (TLC), cooled to RT and THF was removed by evaporation. Water was added and aqueous fractions extracted with EtOAc. The organic fractions were combined, solvent removed and the crude product purified by flash chromatography (Silica gel; hexane/chloroform/EtOAc; gradient up to 20% chloroform then 20% EtOAc) to yield 3-bromo-2,5-bis(4-methoxyphenyl)thiophene (4.9 g, 13 mmol, 65%).

후처리

  1. temperatureThe mixture was refluxed for 16 h (TLC)
  2. customTHF was removed by evaporation
  3. additionWater was added
  4. extractionaqueous fractions extracted with EtOAc
  5. customsolvent removed
  6. customthe crude product purified by flash chromatography (Silica gel

출처 및 근거

ORD 기록
ord-4ad2ec4d58e54e07bd01dbcc2fa5da29
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09176357B2

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