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

HRID 1054230

반응식

HRID 1054230 반응식
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]

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8bae050575614452a28ba348ee0dd43b
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394300B2

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