Methyl morpholine oxide → Methyl 3,5-dibromo-4-formylbenzoate

HRID 394205Notes

Reaction equation

HRID 394205 reaction equation
Br[CH2:2][C:3]1[C:12]([Br:13])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[Br:14].C[N+]1([O-])CC[O:19]CC1>C(#N)C.[Cl-].[Na+].O>[Br:14][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Br:13])[C:3]=1[CH:2]=[O:19])[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22647948Methyl 3,5-dibromo-4-(bromomethyl)benzoate2×

Product 1

HCID 22647908Methyl 3,5-dibromo-4-formylbenzoate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 3,5-dibromo-4-(bromomethyl)benzoate (INTERMEDIATE 24) (3.9 g) was dissolved in acetonitrile (100 mL) and to this was added 4 Å molecular sieves and N-methylmorpholine N-oxide (1.18 g) and the reaction heated to 50° C. for 12 h. The reaction mixture was poured into brine and extracted into ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography eluting with 90% hexane:10% ethyl acetate to give the title compound. 1H NMR (500 MHz, CDCl3): δ 10.27 (s, 1H); 8.29 (s, 2H); 3.99 (s, 3H).

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 90% hexane

Sources & evidence

ORD record
ord-552b45866d3a478b82a8275088fb5393
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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