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

HRID 628577

反応式

HRID 628577 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5c169e95ef9d44dcb933c0b56e040114
出典データセット
uspto-grants-2016_04
特許番号
US09314456B2

関連ノート

読み込み中…