Dimethylformamide → 4'-Chloro-2-nitro-1,1'-biphenyl

HRID 1914405ノート

反応式

HRID 1914405 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 113411-Bromo-2-nitrobenzeneHCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acid

生成物 1

HCID 2355494'-Chloro-2-nitro-1,1'-biphenyl収率 74.4%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

A mixed solution of 10 g of 2-bromonitrobenzene, 8.5 g of 4-chlorophenylboronic acid, 25.4 g of tripotassium phosphate, 3.9 g of tetrabutylammonium bromide, 270 mg of palladium acetate and 150 ml of dimethylformamide was heated and stirred under a nitrogen gas stream at 130° C. for 3 hours. The solution was cooled to room temperature and 100 ml of water was poured into the solution, followed by extraction with 150 ml of ethyl acetate. The organic layer was washed twice with 100 ml of water, dried over magnesium sulfate and then evaporated. The concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 8.6 g of 2-(4-chlorophenyl)nitrobenzene.

後処理

  1. temperatureThe solution was cooled to room temperature
  2. extractionfollowed by extraction with 150 ml of ethyl acetate
  3. washThe organic layer was washed twice with 100 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe concentrate was purified by silica gel column chromatography
  7. customvacuum-dried

出典と根拠

ORDレコード
ord-6f9bb8e249a64b20b03061e29405bb78
出典データセット
uspto-grants-2013_12
特許番号
US08610345B2

反応ノート

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