Sodium Hydroxide → 5-Bromo-6-methoxypyridine-3-carbaldehyde

HRID 2197542Notes

Reaction equation

HRID 2197542 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][N:4]=1.CC([O-])=O.[Na+].[Br:16]Br.[OH-].[Na+]>CC(O)=O.O>[Br:16][C:10]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 517045Sodium AcetateHCID 33645766-Methoxypyridine-3-carbaldehyde

Product 1

HCID 123924165-Bromo-6-methoxypyridine-3-carbaldehydeYield 39.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 6-methoxynicotinaldehyde (3 g, 0.0219 mol) and NaOAc (3.5 g, 0.0427 mol) in HOAc (10 mL) was added a solution of bromine (1.64 mL, 0.031 mol) in HOAc (10 mL) over 30 mins via an additional funnel. The mixture was heated to 90° C. for 5 h, cooled to rt. The reaction was added iced water (100 mL), neutralized to pH=7.5 with aq. NaOH (5 N), extracted with ethyl acetate (4×50 mL), washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified via flash column using dichloromethane as an eluent. The product containing fractions were collected and concentrated to give 5-bromo-6-methoxynicotinaldehyde (1.854 g, 39% yield).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with ethyl acetate (4×50 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via flash column
  8. additionThe product containing fractions
  9. customwere collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-942d22f1c19043a69e8afbb0089bc130
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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