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

HRID 723056

반응식

HRID 723056 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6f20438fc21b46779c5e61664dad14d2
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138530B2

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