Sodium Carbonate → 3'-Chloro-3-nitro-4'-trifluoromethyl-biphenyl-4-ylamine

HRID 2098238노트

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HRID 2098238 반응식
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[C:19]([F:22])([F:21])[F:20].C([O-])([O-])=O.[Na+].[Na+]>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>[Cl:12][C:13]1[CH:14]=[C:15]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)[CH:16]=[CH:17][C:18]=1[C:19]([F:20])([F:21])[F:22]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 701324-Bromo-2-nitroanilineHCID 37729583-Chloro-4-(trifluoromethyl)benzeneboronic acid

생성물 1

HCID 673869773'-Chloro-3-nitro-4'-trifluoromethyl-biphenyl-4-ylamine수율 101.1%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

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온도
95 °C

실험 절차

A mixture of 4-bromo-2-nitroaniline (2.17 g), 3-chloro-4-trifluoromethyl-phenylboronic acid (3.5 g), and Na2CO3 (3.5 g), tetrakis(triphenylphosphine)palladium(0) (0.5 g), in DME (60 mL) and water (60 mL) was degassed under vacuum and the vacuum was broken with N2 gas. The resultant reaction mixture was kept stirring at 90-100° C. for 4 h. The reaction mixture was cooled to room temperature, separated the organic layer and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was dried over sodium sulfate, filtered off sodium sulfate, the filtrate was concentrated and the residue was purified by column chromatography using a silica gel stationary phase and ethyl acetate in hexanes (2:8) as an eluent to afford 3′-chloro-3-nitro-4′-trifluoromethyl-biphenyl-4-ylamine (3.2 g).

후처리

  1. customin DME (60 mL) and water (60 mL) was degassed under vacuum
  2. customThe resultant reaction mixture
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customseparated the organic layer
  5. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
  6. dry with materialThe combined organic layer was dried over sodium sulfate
  7. filtrationfiltered off sodium sulfate
  8. concentrationthe filtrate was concentrated
  9. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-b521901c2dc04e9ba7eed6a2af09a046
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450354B2

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