Water → 4-[(E)-2-(4-bromophenyl)ethenyl]-N,N-dimethyl-aniline

HRID 1430717ノート

反応式

HRID 1430717 の反応式
[CH3:1][O-].[Na+].[Br:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9]P(=O)(OCC)OCC)=[CH:7][CH:6]=1.[CH3:20][N:21]([C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1C=O)[CH3:22].O>CN(C=O)C>[Br:4][C:5]1[CH:6]=[CH:7][C:8](/[CH:9]=[CH:1]/[C:28]2[CH:27]=[CH:24][C:23]([N:21]([CH3:20])[CH3:22])=[CH:30][CH:29]=2)=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 962WaterHCID 34289Benzaldehyde, (dimethylamino)-HCID 10942334Sodium MethoxideHCID 11077666Diethyl (4-Bromobenzyl)phosphonate

生成物 1

HCID 54630864-[(E)-2-(4-bromophenyl)ethenyl]-N,N-dimethyl-aniline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

DMF (anhydrous) (10.5 mL) was added to sodium methoxide (176 mg, 3.26 mmol) and the color was changed to pink. To the above solution diethyl 4-bromobenzylphosphonate (1.0 g, 3.26 mmol) in DMF (6.5 ml) was added dropwise over 2 minutes, followed by 4 (dimethylamino)benzaldehyde (486 mg, 3.26 mmol). The reaction mixture was stirred at room temperature for 24 hours. Deionized water (17 mL) was added. The product was filtered out through vacuum filtration and recrystallized with DCM/hexane to give compound 17. 17: 74%. Yield; tan solid; 1H NMR (400 MHz, CDCl3) δ 7.47-7.32 (m, 6H), 7.04 (d, 1H, J=12.5 Hz), 6.83 (d, 1H, J=16.3 Hz), 6.71 (d, 2H, J=8.9 Hz), 2.99 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 150.5, 137.4, 136.1, 132.1, 131.8, 129.7, 128.3, 128.2, 127.9, 127.7, 125.5, 123.2, 120.3, 112.6, 40.7; HRMS Calc for C16H16BrN 302.0541 found 302.0539.

後処理

  1. filtrationThe product was filtered out through vacuum filtration
  2. customrecrystallized with DCM/hexane

出典と根拠

ORDレコード
ord-ce593aaa37c94be6a5d825f9b6aaf9dc
出典データセット
uspto-grants-2015_01
特許番号
US08940918B2

反応ノート

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