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

HRID 1430717Notes

Reaction equation

HRID 1430717 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-ce593aaa37c94be6a5d825f9b6aaf9dc
Source dataset
uspto-grants-2015_01
Patent number
US08940918B2

Reaction notes

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