Ethanol → 4-Nitro-1,1'-biphenyl

HRID 36721

반응식

HRID 36721 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>COC(OC)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 66827Phenylboronic Acid

생성물 1

HCID 71144-Nitro-1,1'-biphenyl수율 127.3%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8857Ethyl Acetate용매HCID 107951,1-Dimethoxyethane용매

실험 절차

12.50 g (61.9 mmol) of 1-bromo-4-nitrobenzene were added to 358 mg, (310 μmol, 0.5 mole %) of tetrakis (triphenyl-phosphine) palladium in 200 ml of dimethoxy-ethane. After stirring for 10 minutes, 11.3 g (92.8 mmol) of phenylboronic acid and 100 ml of ethanol were added. After a further 10 minutes, 263 ml, (526 mmol, 8.5 equiv) of 2M aqueous sodium carbonate were added and the suspension was heated at reflux for 20 minutes, then allowed to cool to room temperature. The mixture was taken into 250 ml of EtOAc and 200 ml of H2. The aqueous layer was extracted with 200 ml of EtOAc and the combined organics were washed twice with 250 ml of water and 100 ml of brine, dried over MgSO4, filtered and evaporated to obtain 15.7 g of the desired product as a solid.

후처리

  1. waitAfter a further 10 minutes
  2. temperaturethe suspension was heated
  3. temperatureat reflux for 20 minutes
  4. extractionThe aqueous layer was extracted with 200 ml of EtOAc
  5. washthe combined organics were washed twice with 250 ml of water and 100 ml of brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-cde7e681c41a47928ae7eb2e213796e5
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416112

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