Cesium fluoride → 2-fluoro-4-phenylbenzonitrile

HRID 583840ノート

反応式

HRID 583840 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F-].[Cs+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:10][C:4]1[CH:3]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

参加物

6

反応物 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 7360294-Bromo-2-fluorobenzonitrile

生成物 1

HCID 27633602-fluoro-4-phenylbenzonitrile収率 74%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 4-bromo-2-fluorobenzonitrile (1.12 g, 5.6 mmol) in 1,2-dimethoxyethane (10 mL) were added Phenyl boronic acid (750 mg, 6.16 mmol), tetrakis(triphenylphosphine)palladium (0) (194 mg, 0.17 mmol) and Cesium fluoride (1.8 g, 12.3 mmol). The mixture of reaction was stirred at 100° C. under nitrogen for 3 h. Then, the mixture is cooled and filter through celite. Then added ethyl acetate and water and extracted (3×). The crude was purified by chromatography (silica gel, hexane-ethyl acetate 10:1) affordind 818 mg (74% yield)n of the title compound.

後処理

  1. additionThe mixture of reaction
  2. temperatureThen, the mixture is cooled
  3. filtrationfilter through celite
  4. extractionThen added ethyl acetate and water and extracted (3×)
  5. customThe crude was purified by chromatography (silica gel, hexane-ethyl acetate 10:1) affordind 818 mg (74% yield)n of the title compound

出典と根拠

ORDレコード
ord-6b0fab5263ea40428287798687af65bc
出典データセット
uspto-grants-2005_08
特許番号
US06924294B2

反応ノート

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