Potassium Carbonate → HCID 18451489, 화합물

HRID 1270717노트

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HRID 1270717 반응식
[F:1][C:2]1[C:8]([F:9])=[C:7](Br)[C:6]([F:11])=[C:5]([F:12])[C:3]=1[NH2:4].[CH3:13][O:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[C:8]([F:9])=[C:7]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([O:14][CH3:13])[CH:20]=2)[C:6]([F:11])=[C:5]([F:12])[C:3]=1[NH2:4]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 6186714-Bromo-2,3,5,6-tetrafluoroanilineHCID 2734370(3-Methoxyphenyl)boronic acid

생성물 1

HCID 18451489HCID 18451489, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

Alternative procedure: 2,3,5,6-Tetrafluoro-4-bromoaniline (12.0 g, 49.2 mmol) is dissolved in DME (250 mL) and treated with 3-methoxyphenylboronic acid (7.5 g, 49.2 mmol), a catalytic amount of palladium(II) acetate (0.23 g, 1.0 mmol) and tri-o-tolylphosphine (1.22 g, 4.0 mmol). Potassium carbonate (13.6 g in 50 mL water) is added and the reaction mixture stirred, purged with nitrogen, then heated to 90° C. for 24 hours. After cooling to room temperature most of the DME is removed by rotary evaporator under high vacuum. The resulting material is partitioned between EtOAc (200 mL) and water (250 mL). The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator. The crude reaction product is purified by flash chromatography (9:1 hexanes/EtOAc, then 6:4 hexanes/EtOAc) to give 2,3,5,6-tetrafluoro-4-(3′-methoxyphenyl)aniline (m.p. 94–96° C.).

후처리

  1. custompurged with nitrogen
  2. temperatureAfter cooling to room temperature most of the DME
  3. customis removed by rotary evaporator under high vacuum
  4. customThe resulting material is partitioned between EtOAc (200 mL) and water (250 mL)
  5. washThe organic layer is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by rotary evaporator
  8. customThe crude reaction product
  9. customis purified by flash chromatography (9:1 hexanes/EtOAc

출처 및 근거

ORD 기록
ord-2811fa6bb2e04daaa00cb5e2387f1aa1
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202364B2

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