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

HRID 514489ノート

反応式

HRID 514489 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-470cf675cae64eb1bbf473bbe2a1cd1d
出典データセット
uspto-grants-2015_08
特許番号
US09107916B2

反応ノート

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