Phenylboronic Acid → 3-Methoxy-4-nitro-1,1′-biphenyl

HRID 1773494ノート

反応式

HRID 1773494 の反応式
[K].Cl[C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([O:9][CH3:10])[CH:8]=1.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=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].[Cl-].C(C1C=CC=C(C(C)C)C=1[N+]1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C=1)(C)C>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:4]=[CH:5][C:6]=1[N+:11]([O-:13])=[O:12]

参加物

9

反応物 3

HCID 66827Phenylboronic AcidHCID 811105-Chloro-2-nitroanisoleHCID 5462222Potassium

生成物 1

HCID 42831993-Methoxy-4-nitro-1,1′-biphenyl収率 114.8%

試薬・触媒・溶媒 5

HCID 74236Tetrabutylammonium Bromide触媒HCID 27349131,3-Bis(2,6-diisopropylphenyl)imidazolium chloride触媒HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

A solution of potassium methoxyde (0.56 g, 7.98 mmol) in anhydrous methanol (5 mL) was added at 0° C. to a mixture of 5-chloro-2-nitroanisole (0.5 g, 2.66 mmol), phenylboronic acid (0.42 g, 3.44 mmol), bis(dibenzylideneacetone)palladium (47 mg, 0.082 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (35 mg, 0.082 mmol) and tetrabutylammonium bromide (86 mg, 0.267 mmol) in anhydrous toluene (20 mL). The reaction mixture was stirred at 60° C. for 24 hours, and then was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified on a silica gel plug (EtOAc/hexane, 20/80) to give 0.7 g of 3-methoxy-4-nitro-biphenyl as a yellow oil.

後処理

  1. customwas partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified on a silica gel plug (EtOAc/hexane, 20/80)

出典と根拠

ORDレコード
ord-9f3b3890667f4e7baf5e204f2a675e92
出典データセット
uspto-grants-2016_02
特許番号
US09255110B2

反応ノート

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