4-Bromoaniline → HCID 135752757, compound

HRID 1603740Notes

Reaction equation

HRID 1603740 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=O.[Br:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=[N:19][C:18]1[CH:20]=[CH:21][C:15]([Br:14])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 8655Syringaldehyde

Product 1

HCID 135752757HCID 135752757, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,5-Dimethoxy-4-hydroxybenzaldehyde (1 g, 5.46 mmol) was dissolved in methanol (50 ml) and 4-bromoaniline (939 mg, 5.46 mmol) was added. The resultant reaction solution was stirred overnight at room temperature under nitrogen to give a precipitate that was collected by filtration to yield light yellow fine crystals (860 mg) of the title product: 1H NMR (300 MHz, CDCl3); δ 8.30 (S, 1H), 7.49 (d, J=9 Hz, 2H), 7.16 (S, 2H), 7.07 (d, J=9 Hz, 2H), 5.86 (S, 1H), 3.98 (S, 6H).

Workup

  1. customThe resultant reaction solution
  2. customto give a precipitate that
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-1fed3ffbb03f4dae949e8da2704dd67a
Source dataset
uspto-grants-1999_11
Patent number
US05990137

Reaction notes

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