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Dimethyl Sulfoxide → Methyl 5,5'-difluoro-2'-nitrobiphenyl-2-carboxylate

HRID 238073
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HRID 238073 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CS(C)=O.Br[C:17]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]>[F:27][C:25]1[CH:24]=[C:23]([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:26]=1
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참가 물질

7

반응물 3

HCID 679Dimethyl SulfoxideHCID 27569932-Bromo-4-fluoro-1-nitrobenzeneHCID 7210837Methyl 2-bromo-4-fluorobenzoate

생성물 1

HCID 67296874Methyl 5,5'-difluoro-2'-nitrobiphenyl-2-carboxylate수율 113.3%

시약·촉매·용매 3

HCID 23978Copper촉매
HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To 2-bromo-4-fluoro-1-nitrobenzene (185.16 mg, 0.842 mmol) was added Pd2 dba3 (23.12 mg, 0.025 mmol) and copper powder (271 mg, 4.26 mmol). Dimethylsulfoxide (2.3 ml) and methyl 2-bromo-4-fluorobenzoate (0.122 ml, 0.842 mmol) were added and the mixture was stirred vigorously at 100° C. for 2 h. The mixture was cooled to room temperature, diluted with ethyl acetate (20 ml), and filtered. The filtrate was washed with water and dried (anhydrous Na2SO4) and concentrated to give a yellow oil (279.8 mg). This oil was utilized without purification for the preparation of Example 38b.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with water
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8bf63440aae5492c821e7b955315aad5
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642538B2

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