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

HRID 1773494노트

반응식

HRID 1773494 반응식
[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]

참가 물질

9

반응물 3

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

생성물 1

HCID 42831993-Methoxy-4-nitro-1,1′-biphenyl수율 114.8%

시약·촉매·용매 5

HCID 74236Tetrabutylammonium Bromide촉매HCID 27349131,3-Bis(2,6-diisopropylphenyl)imidazolium chloride촉매HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 887Methanol용매HCID 1140Toluene용매

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온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9f3b3890667f4e7baf5e204f2a675e92
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255110B2

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