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

HRID 1052919ノート

反応式

HRID 1052919 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 95.1%

試薬・触媒・溶媒 3

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

実験手順

A mixed solution of 20 g of 2-bromonitrobenzene, 17 g of 4-chlorophenylboronic acid, 45 g of tripotassium phosphate, 6.9 g of tetrabutylammonium bromide, 480 mg of palladium acetate and 500 ml of dimethylformamide was heated/stirred at 130° C. for 5 hours under a nitrogen flow. The solution was cooled to room temperature, then poured into 100 ml of water, and extracted with 150 ml of toluene. The organic layer was washed with 100 ml of water three times, dried over magnesium sulfate, and then evaporated. The concentrate was purified by silica gel column chromatography and vacuum-dried to obtain 22 g of 2-(4-chlorophenyl)nitrobenzene.

後処理

  1. extractionextracted with 150 ml of toluene
  2. washThe organic layer was washed with 100 ml of water three times
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe concentrate was purified by silica gel column chromatography
  6. customvacuum-dried

出典と根拠

ORDレコード
ord-cbdac8bfae2047ab85d1e4fae43dd1e5
出典データセット
uspto-grants-2016_07
特許番号
US09391288B2

反応ノート

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