Potassium Phosphate, Tribasic → Ethyl 4-nitro-[1,1'-biphenyl]-3-carboxylate

HRID 1054230ノート

反応式

HRID 1054230 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:13]([C:5]1[CH:4]=[CH:3][C:2]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-:15])=[O:14]

参加物

8

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 603450Ethyl 5-chloro-2-nitrobenzoate

生成物 1

HCID 90258855Ethyl 4-nitro-[1,1'-biphenyl]-3-carboxylate収率 89%

試薬・触媒・溶媒 4

HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
95 °C

実験手順

To a stirring solution of ethyl 5-chloro-2-nitrobenzoate (2 g, 8.71 mmol) and phenylboronic acid (2.124 g, 17.42 mmol) in DMF (20 ml) was added K3PO4 (2.77 g, 13.07 mmol), palladium acetate (0.098 g, 0.436 mmol) and tetrabutylammonium bromide (4.21 g, 13.07 mmol). Reaction mixture was heated at 95° C. for 16 h. Reaction mixture was diluted with water and extracted with EtOAc. The organic layer was separated and distilled out to get crude product which was column purified using 10% EtOAC in hexane to get the titled compound in 89% yield.

後処理

  1. customReaction mixture
  2. customReaction mixture
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. distillationdistilled out
  6. customto get crude product which
  7. custompurified

出典と根拠

ORDレコード
ord-8bae050575614452a28ba348ee0dd43b
出典データセット
uspto-grants-2016_07
特許番号
US09394300B2

反応ノート

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