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Dimethylformamide → Methyl 2'-fluoro-5'-(methyloxy)-2-nitro-1,1'-biphenyl-4-carboxylate

HRID 404342
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HRID 404342 반응식
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].CN(C=O)C.[F:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]
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7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 735797Methyl 4-chloro-3-nitrobenzoateHCID 41572112-Fluoro-5-methoxyphenylboronic acid

생성물 1

HCID 57706335Methyl 2'-fluoro-5'-(methyloxy)-2-nitro-1,1'-biphenyl-4-carboxylate수율 99%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 57417360Sodium chloride; water용매

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온도
90 °C

실험 절차

To a stirred solution of methyl 4-chloro-3-nitrobenzoate (10.00 g, 46 mmol, commercially available from TCI) in DMF (15.00 mL, 194 mmol) at 23° C. was added 2-fluoro-5-methoxyphenylboronic acid (12 g, 70 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), potassium carbonate (19 g, 139 mmol), and then tetrakis(triphenylphosphine)palladium (2.1 g, 1.9 mmol). The mixture was heated at 90° C. for 18 hours and then cooled to room temperature. The reaction was diluted with brine and extracted three times with EtOAc. The organic layers were combined, dried over anhydrous MgSO4, and filtered. The organic solvent was removed under reduced pressure and the residue was purified on silica gel (0-40% EtOAc in hexanes) to yield T12.3 as a colorless oil (14.00 g, 99% yield).

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted three times with EtOAc
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe organic solvent was removed under reduced pressure
  6. customthe residue was purified on silica gel (0-40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-0e3180df4ea746a5a105839c707d01c2
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748462B2

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