Vinyl Acetate → 4-Bromo-1-chloro-2-(4-(2-(vinyloxy)ethyl)benzyl)benzene

HRID 2403762ノート

反応式

HRID 2403762 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([CH:17]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:25](OC=C)(=O)[CH3:26]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][O:16][CH:25]=[CH2:26])=[CH:10][CH:9]=2)[CH:17]=1

参加物

6

反応物 3

HCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 595577662-(4-(5-Bromo-2-chlorobenzyl)phenyl)ethanol

生成物 1

HCID 595577724-Bromo-1-chloro-2-(4-(2-(vinyloxy)ethyl)benzyl)benzene収率 86.7%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-(4-(5-bromo-2-chlorobenzyl)phenyl)ethanol (intermediate BH) (500 mg, 1.46 mmol), [IrCl(cod)]2 (9.8 mg, 0.015 mmol) and sodium carbonate (93 mg, 0.87 mmol) in toluene (2 mL) was added vinyl acetate (0.27 mL, 2.91 mmol) under argon. The reaction mixture was heated to 100° C. and stirred for 2 h. The solution was allowed to cool to room temperature, and then diluted with 50 mL of ethyl acetate. The mixture was washed with water (20 mL) and then with brine (20 mL), and dried over sodium sulfate. The residue was concentrated and purified by column chromatography (eluent EA:PE:Et3N=1:20:0.01) to provide 445 mg of yellow solid. 1H-NMR (CDCl3, 400 MHz): δ 7.22˜7.14 (m, 3H), 7.10 (d, 2H), 7.04 (d, 2H), 6.40 (dd, J=14.4 and 6.8 Hz, 1H), 4.11 (dd, J=14.4 and 2.0 Hz, 1H), 3.96 (s, 2H), 3.93 (dd, J=6.8 and 2.0 Hz, 1H), 3.82 (t, J=7.2 Hz, 2H), 2.88 (t, J=7.2 Hz, 2H).

後処理

  1. temperatureto cool to room temperature
  2. washThe mixture was washed with water (20 mL)
  3. dry with materialwith brine (20 mL), and dried over sodium sulfate
  4. concentrationThe residue was concentrated
  5. custompurified by column chromatography (eluent EA:PE:Et3N=1:20:0.01)

出典と根拠

ORDレコード
ord-96a771943bc54af388e67c7aa7705a94
出典データセット
uspto-grants-2014_08
特許番号
US08802637B2

反応ノート

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