3-Fluorophenylboronic acid → 1-(6-Bromo-4-chloro-3'-fluoro-5-methylbiphenyl-2-yl)ethanone

HRID 510887ノート

反応式

HRID 510887 の反応式
[Na].FC(F)(F)S(O[C:8]1[C:13]([C:14](=[O:16])[CH3:15])=[CH:12][C:11]([Cl:17])=[C:10]([CH3:18])[C:9]=1[Br:19])(=O)=O.[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1>O.C1(C)C=CC=CC=1.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>[Br:19][C:9]1[C:8]([C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([F:22])[CH:28]=2)=[C:13]([C:14](=[O:16])[CH3:15])[CH:12]=[C:11]([Cl:17])[C:10]=1[CH3:18]

参加物

7

反応物 3

HCID 27339863-Fluorophenylboronic acidHCID 5360545SodiumHCID 866667866-Acetyl-2-bromo-4-chloro-3-methylphenyl trifluoromethanesulfonate

生成物 1

HCID 885361331-(6-Bromo-4-chloro-3'-fluoro-5-methylbiphenyl-2-yl)ethanone収率 93%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a solution of sodium hydrogenecarbonate (0.21 g, 2.5 mmol) in water (5 mL) was added a solution of 6-acetyl-2-bromo-4-chloro-3-methylphenyl trifluoromethanesulfonate (0.50 g, 1.3 mmol) in toluene (5 mL) followed by (3-fluorophenyl)boronic acid (0.21 g, 1.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (75 mg, 0.065 mmol). The mixture was bubbled with N2 for 5 min and then heated at 80° C. overnight. The reaction was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and purified on silica gel (eluting with 0-20% of ethyl acetate in hexanes) to give the desired product (0.40 g, 93%). LCMS calculated for C15H12BrClFO (M+H)+: m/z=341.0. found: 341.0.

後処理

  1. customThe mixture was bubbled with N2 for 5 min
  2. additionThe reaction was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified on silica gel (eluting with 0-20% of ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-4ce13a25573e4a2aacd268309aecb645
出典データセット
uspto-grants-2015_08
特許番号
US09096600B2

反応ノート

読み込み中…