Bromine → 5-Bromo-6-methoxy-2-naphthaldehyde

HRID 1357268Notes

Reaction equation

HRID 1357268 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH:15]=[O:16])[CH:9]=[CH:8]2>CC(O)=O>[Br:1][C:6]1[C:5]([O:4][CH3:3])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([CH:15]=[O:16])=[CH:11]2

Participants

4

Reactant 2

HCID 24408BromineHCID 769916-Methoxy-2-naphthaldehyde

Product 1

HCID 185053535-Bromo-6-methoxy-2-naphthaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (556 μL, 10.8 mL) in 10 mL of glacial HOAc was added under nitrogen dropwise over 1 h to a solution of 6-methoxy-naphthalene-2-carbaldehyde (2.01 g, 10.8 mmol) in 25 mL of glacial HOAc at room temperature. After the addition the reaction was stirred at room temperature for 2 h. The solid was collected by filtration, rinsed with glacial HOAc and dried under reduced pressure to give 5-bromo-6-methoxy-naphthalene-2-carbaldehyde (2.27 g, 79%) as a tan solid, mp 148-150° C.

Workup

  1. additionAfter the addition the reaction
  2. filtrationThe solid was collected by filtration
  3. washrinsed with glacial HOAc
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-af5a5595c4eb49c081aab7aa48385f0c
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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