HCID 58001782, compound → 5-Bromo-6-(trifluoromethyl)nicotinaldehyde

HRID 420750Notes

Reaction equation

HRID 420750 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[N:6][C:7]=1[C:8]([F:11])([F:10])[F:9]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[O:13])[CH:5]=[N:6][C:7]=1[C:8]([F:9])([F:10])[F:11]

Participants

3

Reactant 1

HCID 58001782HCID 58001782, compound

Product 1

HCID 580017775-Bromo-6-(trifluoromethyl)nicotinaldehydeYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of [5-bromo-6-(trifluoromethyl)-3-pyridinyl]methanol (155 mg, 0.605 mmol) in DCM (10 mL) was added CrO2 (Magtrieve) (1017 mg, 12.11 mmol). The suspension was heated at 40° C. in a pressure tube overnight. TLC showed starting material remaining, an excess of CrO2 (254 mg, 3.03 mmol) was added. The reaction mixture was heated at 40° C. for 4 h. The suspension was filtered over nylon membrane 0.45 μm and it was rinsed with DCM. The filtrate was evaporated under vacuum to afford 120 mg (78%) of title compound pure enough to be used in the next step.

Workup

  1. temperatureThe reaction mixture was heated at 40° C. for 4 h
  2. filtrationThe suspension was filtered over nylon membrane 0.45 μm and it
  3. washwas rinsed with DCM
  4. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-fbc19fcb4ded4e4e8441adb639953a80
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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