Pyridine → N-(1,3-dibromodibenzo[b,d]furan-4-yl)acetamide

HRID 1750917Notes

Reaction equation

HRID 1750917 reaction equation
[Br:1][C:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[O:7][C:6]=2[C:5]([NH2:15])=[C:4]([Br:16])[CH:3]=1.N1C=CC=CC=1.[C:23](Cl)(=[O:25])[CH3:24]>ClCCl>[Br:1][C:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[O:7][C:6]=2[C:5]([NH:15][C:23](=[O:25])[CH3:24])=[C:4]([Br:16])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 584010661,3-Dibromodibenzo[b,d]furan-4-amine

Product 1

HCID 58400857N-(1,3-dibromodibenzo[b,d]furan-4-yl)acetamideYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 2 L round-bottomed flask, 1,3-dibromodibenzo[b,d]furan-4-amine (76 g, 223 mmol) in dichloromethane (800 mL) and pyridine (180 mL, 2229 mmol) were cooled by ice bath. Acetyl chloride (31.7 mL, 446 mmol) was added dropwise while stirring. Then the ice bath was removed. The reaction was stirred at room temperature for 1 h. The residue was collected by filtration and washed by water and dichloromethane to give N-(1,3-dibromodibenzo[b,d]furan-4-yl)acetamide (60 g, 70.3% yield) as brown solid.

Workup

  1. customThen the ice bath was removed
  2. stirringThe reaction was stirred at room temperature for 1 h
  3. filtrationThe residue was collected by filtration
  4. washwashed by water and dichloromethane

Sources & evidence

ORD record
ord-61240f818c4c40c08651ddf6cc23109d
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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