Triethylamine → 2,2,2-Trifluoro-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)ethanol

HRID 2216009

反応式

HRID 2216009 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][CH:7]=1.[CH3:14][C:15]1([CH3:22])[C:19]([CH3:21])([CH3:20])[O:18][BH:17][O:16]1.CCN(CC)CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:10][C:9]([F:12])([F:11])[CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([B:17]2[O:18][C:19]([CH3:21])([CH3:20])[C:15]([CH3:22])([CH3:14])[O:16]2)[CH:3]=1)[OH:13]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 146474423'-Bromo-2,2,2-trifluoroacetophenone

生成物 1

HCID 218861552,2,2-Trifluoro-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)ethanol収率 53%

試薬・触媒・溶媒 1

HCID 178418476HCID 178418476、化合物触媒

反応条件

温度
95 °C

実験手順

To an oven-dried round bottom flask fitted with a stir bar and a rubber septum was added 1-(3-bromo-phenyl)-2,2,2-trifluoro-ethanone (560 mg, 2.2 mmol, as prepared in Example 28, step a), 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (0.96 mL, 6.6 mmol, Aldrich Chemical Company), (PPh3)2PdCl2 (93 mg, 0.132 mmol, Strem Chemicals, Inc., Newburyport, Mass.), and Et3N (1.8 mL, 13.2 mmol). The reaction mixture was evacuated, purged with argon, and then suspended in dioxane (16 mL). After stirring for 18 hr at 95° C., the reaction was allowed to cool and then filtered through Celite.® The filtrate was concentrated in vacuo and the residue was purified by chromatography (SiO2, flash elution: 5% EtOAc in hexanes) to give 350 mg (53%) of an oil that was used without further purification.

後処理

  1. customTo an oven-dried round bottom flask fitted with a stir bar
  2. customThe reaction mixture was evacuated
  3. custompurged with argon
  4. temperatureto cool
  5. filtrationfiltered through Celite
  6. concentration® The filtrate was concentrated in vacuo
  7. customthe residue was purified by chromatography (SiO2, flash elution: 5% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-1c111f7200ef44e287b880dfd8f2178d
出典データセット
uspto-grants-2006_09
特許番号
US07109354B2

関連ノート

読み込み中…