Potassium Carbonate → HCID 18451489、化合物

HRID 1270716

反応式

HRID 1270716 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 18451489HCID 18451489、化合物

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
90 °C

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-c0a8c1fe4a3c4fe9b0f239282dd887b2
出典データセット
uspto-grants-2007_04
特許番号
US07202364B2

関連ノート

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