1-Naphthaldehyde → 6-Bromonaphthalene-1-carbaldehyde

HRID 860563Notes

Reaction equation

HRID 860563 reaction equation
[C:1]1([CH:11]=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:13]Br>C(Cl)(Cl)Cl>[Br:13][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[C:1]([CH:11]=[O:12])=[CH:2][CH:3]=[CH:4]2

Participants

4

Reactant 2

HCID 61951-NaphthaldehydeHCID 24408Bromine

Product 1

HCID 131424516-Bromonaphthalene-1-carbaldehydeYield 36.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a flask fitted with a condenser containing 1-naphthaldehyde (10 g, 64.02 mmol) was added a solution of bromine (3.3 mL, 63.83 mmol) in anhydrous chloroform (15 mL). The reaction mixture was heated under reflux for 3.5, allowed to RT and filtered. The filtrate was washed with water, brine and dried (MgSO4). After evaporation the crude product was purified on silica gel (eluant: hexanes:EtOAc, 98:2) to afford 6-bromo-1-naphthaldehyde 5.5 g (27%).

Workup

  1. customTo a flask fitted with a condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 3.5
  4. customallowed to RT
  5. filtrationfiltered
  6. washThe filtrate was washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customAfter evaporation the crude product
  9. customwas purified on silica gel (eluant: hexanes:EtOAc, 98:2)

Sources & evidence

ORD record
ord-3f81eafd0b224bd48cc62fa725adc873
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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