Water → 6-Chloro-3'-fluorobiphenyl-3-ol

HRID 1619701ノート

反応式

HRID 1619701 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1I.[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.O>O1CCOCC1>[Cl:7][C:8]1[C:9]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([F:16])[CH:22]=2)=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27339863-Fluorophenylboronic acidHCID 229287294-Chloro-3-iodophenol

生成物 1

HCID 580422636-Chloro-3'-fluorobiphenyl-3-ol収率 100%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

Caesium carbonate (1.15 g, 3.53 mmol) was added to a solution of 4-chloro-3-iodophenol (300 mg, 2.14 mmol) and 3-fluorophenylboronic acid (330 mg, 1.30 mmol) in dioxane:water (22.5 mL:4.5 mL). The reaction mixture was degassed and tetrakistriphenylphosphine palladium (0) (69 mg, 0.06 mmol) was added. The reaction mixture was stirred at 70° C. for 5 hours. The cooled reaction mixture was concentrated in vacuo and the aqueous residue was extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified on the biotage eluting with heptane:ethyl acetate (from 98:2 to 80:20) to give the title compound (270 mg, 100%) as a yellow solid.

後処理

  1. customThe reaction mixture was degassed
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. extractionthe aqueous residue was extracted with ethyl acetate (3×10 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on the biotage
  9. washeluting with heptane

出典と根拠

ORDレコード
ord-86e26e158b3c4c0ab239898d9097551e
出典データセット
uspto-grants-2014_07
特許番号
US08772293B2

反応ノート

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