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

HRID 1430717노트

반응식

HRID 1430717 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-ce593aaa37c94be6a5d825f9b6aaf9dc
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940918B2

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