Water → 2-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanone

HRID 1751529노트

반응식

HRID 1751529 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:25]=1)=[CH:12][CH:13]=[C:14]1[C:19]=2[O:18][CH2:17][C:16]2[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:15]1=2)(=O)=O.C([Sn](CCCC)(CCCC)[C:33]([O:35]CC)=[CH2:34])CCC.O.[Br:47]N1C(=O)CCC1=O>CN(C)C=O.ClCCl.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:47][CH2:35][C:33]([C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:25]=1)=[CH:12][CH:13]=[C:14]1[C:19]=2[O:18][CH2:17][C:16]2[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:15]1=2)=[O:34]

참가 물질

8

반응물 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 867087538-bromo-6H-dibenzo[c,h]chromen-2-yl trifluoromethanesulfonate

생성물 1

HCID 867087542-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanone수율 70.5%

시약·촉매·용매 3

HCID 11071931Dichloropalladium--(ethane-1,2-diyl)bis(diphenylphosphane) (1/1)촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

A solution of 8-bromo-6H-dibenzo[c,h]chromen-2-yl trifluoromethanesulfonate (780 mg, 1.7 mmol) and tributyl(1-ethoxyvinyl)stannane (0.86 mL, 2.6 mmol) in dimethylformamide was degassed with a stream of argon for 15 minutes. PdCl2(dppe) (50 mg, 0.086 mmol) was added and the reaction was stirred at room temperature. After 30 hours, water (1 mL) and N-bromosuccinimide (756 mg, 4.2 mmol) were sequentially added to the reaction. After stirring for 2.5 hours at room temperature the reaction was diluted with dichloromethane. The organics were washed with 5% aqueous LiCl solution, saturated aqueous NaHCO3 solution, and brine. After the organic layer was dried (Na2SO4) and concentrated, the crude material was recrystallized from dichloromethane and hexanes to yield 2-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanone (518 mg, 57%).

후처리

  1. stirringAfter stirring for 2.5 hours at room temperature the reaction
  2. washThe organics were washed with 5% aqueous LiCl solution, saturated aqueous NaHCO3 solution, and brine
  3. dry with materialAfter the organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe crude material was recrystallized from dichloromethane and hexanes

출처 및 근거

ORD 기록
ord-6f84fc2e1150415b8872acdfd91b5397
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156823B2

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