Potassium Phosphate, Tribasic → N4-Methyl-3,3'-dinitrobiphenyl-4,4'-diamine

HRID 873345

반응식

HRID 873345 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[N+:13]([C:16]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[CH:19][C:17]=1[NH2:18])([O-:15])=[O:14].C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.O>[CH3:7][NH:6][C:5]1[CH:8]=[CH:9][C:2]([C:21]2[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([N+:13]([O-:15])=[O:14])[CH:22]=2)=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

참가 물질

6

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 2580424-Bromo-N-methyl-2-nitroanilineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 162179142-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

생성물 1

HCID 86661422N4-Methyl-3,3'-dinitrobiphenyl-4,4'-diamine수율 169.4%

시약·촉매·용매 1

HCID 18180031Water 1,2-dimethoxyethane용매

반응 조건

온도
130 °C

실험 절차

4-Bromo-N-methyl-2-nitroaniline (100 mg, 0.43 mmol), 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (115 mg, 0.43 mmol), biphenyl-2-yldicyclohexylphosphine (30 mg, 20 mol %) and K3PO4 (275 mg, 1.3 mmol) were suspended in DME-H2O (4:1, 5 mL). the mixture was purged with nitrogen then degassed by sonication. Pd(OAc)2 (5 mg, 5 mol %) was added, and the mixture heated to 130° C. for 10 min under microwave irradiation. The cooled mixture was diluted with EtOAc and H2O. The organics were separated and the aqueous layer extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give the crude product as a dark brown solid (210 mg). The crude material was taken on without further purification.

후처리

  1. customthe mixture was purged with nitrogen
  2. customthen degassed by sonication
  3. additionPd(OAc)2 (5 mg, 5 mol %) was added
  4. additionThe cooled mixture was diluted with EtOAc and H2O
  5. customThe organics were separated
  6. extractionthe aqueous layer extracted with EtOAc (3×50 mL)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-eeaa658dcc084faaac5484efb8a44951
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975416B2

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