Water → Ethyl 3-(3,5-dibromo-4-(4-methoxybenzyloxy)phenyl)-1,2,4-oxadiazole-5-carboxylate

HRID 2402273Notes

Reaction equation

HRID 2402273 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:12]2[N:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[O:14][N:13]=2)[CH:7]=[C:8]([Br:11])[C:9]=1[OH:10].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1.O>CN(C)C=O>[Br:3][C:4]1[CH:5]=[C:6]([C:12]2[N:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[O:14][N:13]=2)[CH:7]=[C:8]([Br:11])[C:9]=1[O:10][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 136139598Ethyl 3-(3,5-dibromo-4-hydroxyphenyl)-1,2,4-oxadiazole-5-carboxylate

Product 1

HCID 57919720Ethyl 3-(3,5-dibromo-4-(4-methoxybenzyloxy)phenyl)-1,2,4-oxadiazole-5-carboxylateYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (100 mg of a 60% suspension in oil, 2.5 mmol) was added to a stirred solution of ethyl 3-(3,5-dibromo-4-hydroxyphenyl)-1,2,4-oxadiazole-5-carboxylate (980 mg, 2.5 mmol) in dry dimethylformamide (5 mL) under nitrogen and the mixture was stirred at room temperature for 15 minutes. 4-Methoxybenzyl chloride (470 mg, 3.0 mmol) was added and the resulting solution was stirred at 50° C. for 20 h. The cooled mixture was treated with water (10 mL) to give a colourless solid that was filtered, washed with water and dried. Crystallization from di-isopropyl ether gave the title compound (840 mg, 65%) as a colourless powder. 1H NMR δ (ppm) (DMSO-d6): 1.41 (3 H, t), 3.52 (3 H, s), 4.49 (2 H, t), 5.06 (2 H, s), 7.01 (2 H, d), 7.53 (2H, d), 8.30 (2H, s).

Workup

  1. stirringthe resulting solution was stirred at 50° C. for 20 h
  2. customto give a colourless solid
  3. filtrationthat was filtered
  4. washwashed with water
  5. customdried
  6. customCrystallization from di-isopropyl ether

Sources & evidence

ORD record
ord-ce79363d501d477fb5acb91b43068b77
Source dataset
uspto-grants-2014_08
Patent number
US08796321B2

Reaction notes

Loading…