Diethyl Ether → 4-Methoxy-2-nitro-biphenyl

HRID 617405ノート

反応式

HRID 617405 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].CCOCC>C(COC)OC.[Cl-].[Na+].O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

参加物

8

反応物 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 792884-Bromo-3-nitroanisole

生成物 1

HCID 114019374-Methoxy-2-nitro-biphenyl収率 44%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒2 回HCID 80711,2-Dimethoxyethane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A magnetically stirred suspension of 4-bromo-3-nitroanisole (64.41 g, 278 mmol), phenylboronic acid (36.15 g, 296 mmol), and tris(dibenzylideneacetone)dipalladium(0) in dimethoxyethane (375 mL)/2 N sodium carbonate solution (517 mL) was stirred for 3 d under nitrogen. Additional tris(dibenzylideneacetone)-dipalladium(0) (0.5 g) was added and the suspension was stirred for 12 h, treated with Et2O (200 mL) and brine (200 mL), and the layers were separated. The aqueous layer was further extracted with fresh Et2O (2×300 mL), the combined organic extracts were filtered through Celite with diethyl ether elution, washed with water (500 mL) and brine (500 mL), dried (K2CO3), filtered, and concentrated in vacuo to afford 27.89 g (44%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 3.88 (s, 3H), 7.12 (dd, J=8, 2 Hz, 1H), 7.23-7.29 (m, 2H), 7.32-7.42 (m, 5H).

後処理

  1. stirringthe suspension was stirred for 12 h
  2. customthe layers were separated
  3. extractionThe aqueous layer was further extracted with fresh Et2O (2×300 mL)
  4. filtrationthe combined organic extracts were filtered through Celite with diethyl ether elution
  5. washwashed with water (500 mL) and brine (500 mL)
  6. dry with materialdried (K2CO3)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-baf521aabdc94c1e9fd477bb995d4f9f
出典データセット
uspto-grants-1999_09
特許番号
US05948817

反応ノート

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