Sodium Carbonate → 5-Bromo-2-fluoro-2',3'-dimethoxy-2''-fluoro-p-terphenyl

HRID 470726ノート

反応式

HRID 470726 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[C:10]([O:17][CH3:18])[C:9]=1[O:19][CH3:20].[F:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=1I.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:28][C:25]1[CH:24]=[CH:23][C:22]([F:21])=[C:27]([C:11]2[CH:12]=[CH:13][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[C:9]([O:19][CH3:20])[C:10]=2[O:17][CH3:18])[CH:26]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 677757472'-Fluoro-2,3-dimethoxybiphenyl-4-boronic acid

生成物 1

HCID 677757275-Bromo-2-fluoro-2',3'-dimethoxy-2''-fluoro-p-terphenyl収率 80.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

In the atmosphere of argon, 15.2 g of 2′-fluoro-2,3-dimethoxybiphenyl-4-boronic acid, 16.5 g of 2-fluoro-5-bromoiodobenzene, 1.27 g of tetrakistriphenylphosphine palladium (0), 180 mL of toluene and 90 mL of an aqueous 2M sodium carbonate solution were placed in a flask. The resulting solution was stirred with heating under reflux for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate, and concentrated. Residues were purified by means of silica gel column chromatography, whereby 17.8 g (yield: 80%) of 5-bromo-2-fluoro-2′,3′-dimethoxy-2″-fluoro-p-terphenyl was obtained.

後処理

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hours
  3. extractionthe reaction solution was extracted with toluene
  4. customAn aqueous phase was removed
  5. washan organic phase was washed with saturated saline
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. concentrationconcentrated
  8. customResidues were purified by means of silica gel column chromatography

出典と根拠

ORDレコード
ord-cef7121a837d4c3ebbcc09e0f5207a00
出典データセット
uspto-grants-2014_01
特許番号
US08629430B2

反応ノート

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