1,4-Dibromobutane → HCID 59474963, compound

HRID 2036552Notes

Reaction equation

HRID 2036552 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:20][CH2:21][CH2:22][CH2:23][CH2:24]Br>CC(C)=O>[Br:20][CH2:21][CH2:22][CH2:23][CH2:24][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 59474959HCID 59474959, compound

Product 1

HCID 59474963HCID 59474963, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-hydroxy-2-nitrobenzamide 3 (0.7 g, 0.0038 mol) in 20 mL acetone was added potassium carbonate (2.0 g, 0.015 mol). The reaction mixture was stirred at room temperature for 10 min. Then 1,4-dibromobutane 4 (1.8 mL, 0.015 mol) was added. The resulting mixture was refluxed for 12 h. The progress of the reaction was monitored by thin layer chromatography (TLC). Potassium carbonate was filtered and washed with acetone. The combined filtrate and washings were evaporated. The residue was triturated with methyl tert-butyl ether; the solid separated was filtered and dried to give 4-(4-bromobutoxy)-2-nitrobenzamide 5. White solid (0.85 g, 70%). 1H NMR (400 MHz, CDCl3): δ 1.98-2.03 (m, 2H); 2.04-2.09 (m, 2H); 3.49 (t, J=6.0 Hz, 2H); 4.08 (t, J=5.2 Hz, 2H); 5.80 (br s, 2H); 7.13 (dd, J=2.4, 8.4 Hz, 1H); 7.47-7.52 (m, 2H).

Workup

  1. temperatureThe resulting mixture was refluxed for 12 h
  2. filtrationPotassium carbonate was filtered
  3. washwashed with acetone
  4. customThe combined filtrate and washings were evaporated
  5. customThe residue was triturated with methyl tert-butyl ether
  6. customthe solid separated
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-87a7eca8e9f74773a06a8ccf9e7a32cd
Source dataset
uspto-grants-2013_11
Patent number
US08575185B2

Reaction notes

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