Triethylamine → [4-fluoro-2-[(E)-2-(4-fluorophenyl)ethenyl]phenyl]methanol

HRID 514489노트

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HRID 514489 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[CH2:19])=[CH:14][CH:13]=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.CN(C=O)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][OH:10])=[C:2](/[CH:19]=[CH:18]/[C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)[CH:7]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 678834-FluorostyreneHCID 2773347(2-Bromo-4-fluorophenyl)methanol

생성물 1

HCID 86725608[4-fluoro-2-[(E)-2-(4-fluorophenyl)ethenyl]phenyl]methanol수율 50%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

Charged (2-bromo-4-fluorophenyl)methanol (954 mg, 4.65 mmol), 4-fluoro-1-vinylbenzene (1.14 g, 9.31 mmol), Pd(PPh3)2Cl2 (49 mg, 0.07 mmol), Et3N (942 mg, 9.31 mmol) and DMF (5 mL) to a sealed tube, the mixture was then purged with nitrogen, heated to 150° C. for 3 h in microwave oven. The reaction mixture was filtered, the filtrate was then extracted with ethyl acetate, concentrated and purified by flash column chromatograph to give 569 mg of the title compound (50%). 1H NMR (400 MHz, CDCl3): δ 1.60 (1H, t, J=6.4 Hz), 4.78 (2H, d, J=6.4 Hz), 6.93-7.08 (4H, m), 7.31-7.35 (3H, m), 7.48-7.52 (2H, m).

후처리

  1. customthe mixture was then purged with nitrogen
  2. filtrationThe reaction mixture was filtered
  3. extractionthe filtrate was then extracted with ethyl acetate
  4. concentrationconcentrated
  5. custompurified by flash column chromatograph

출처 및 근거

ORD 기록
ord-470cf675cae64eb1bbf473bbe2a1cd1d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107916B2

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