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

HRID 238073

反応式

HRID 238073 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8bf63440aae5492c821e7b955315aad5
出典データセット
uspto-grants-2014_02
特許番号
US08642538B2

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