Hydrochloric Acid → 3,5-Dibromobenzaldehyde

HRID 378163

Reaction equation

HRID 378163 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[CH2:5]Br.C1N2CN3CN(C2)CN1C3.Cl.[OH2:22]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[CH:5]=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 4101HexamethylenetetramineHCID 1434273,5-Dibromobenzyl bromide

Product 1

HCID 6220773,5-Dibromobenzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 3,5-dibromobenzylbromide (Lancaster) (20 g, 0.061 mole) in H2O (27 mL) and glacial acetic acid (27 mL) was added hexamethylenetetramine (Aldrich). The reaction mixture was heated at reflux for 2 hours. Concentrated HCl (22 mL) was then added and the refluxing was continued for 30 minutes. After cooling to room temperature, the reaction mixture was poured into H2O (230 mL) and stirred for 10 minutes. The resulting precipitate was filtered, washed with H2O and dried to yield 3,5-dibromobenzaldehyde (11.45 g) as a white solid. MS and NMR were consistent with the desired structure.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-f3c898486bb044c3a3b6b92432ed6315
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Linked notes

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