Potassium Carbonate → HCID 18451489, 화합물

HRID 1270716

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HRID 1270716 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(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[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

6

반응물 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 6186714-Bromo-2,3,5,6-tetrafluoroanilineHCID 2734370(3-Methoxyphenyl)boronic acid

생성물 1

HCID 18451489HCID 18451489, 화합물

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
90 °C

실험 절차

2,3,5,6-Tetrafluoro-4-bromoaniline (7.5 g, 30.7 mmol) is dissolved in DME (150 mL) and treated with 3-methoxyphenylboronic acid (4.7 g, 30.7 mmol), a catalytic amount of tetrakistriphenylphosphine palladium(0) (0.70 g, 0.6 mmol) and triphenylphosphine (0.66 g, 2.5 mmol). Potassium carbonate (8.5 μg in 50 mL of water) is added and the reaction mixture stirred and 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. customis removed by rotary evaporator under high vacuum
  2. customThe resulting material is partitioned between EtOAc (200 mL) and water (250 mL)
  3. washThe organic layer is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by rotary evaporator
  6. customThe crude reaction product
  7. customis purified by flash chromatography (9:1 hexanes/EtOAc

출처 및 근거

ORD 기록
ord-c0a8c1fe4a3c4fe9b0f239282dd887b2
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202364B2

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