4-Hydroxybenzaldehyde → HCID 28875386, compound

HRID 474647Notes

Reaction equation

HRID 474647 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[F:9][C:8]([F:11])([F:10])[C:4]1[N:3]=[C:2]([O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 6023342-Chloro-6-(trifluoromethyl)pyridine

Product 1

HCID 28875386HCID 28875386, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2-chloro-6-(trifluoromethyl)pyridine (1.5 g, 8.26 mmol) and 4-hydroxybenzaldehyde (1.009 g, 8.26 mmol) in DMF (18 mL), was added K2CO3 (1.713 g, 12.39 mmol). The mixture was heated at 130° C. for 5 h, and then transferred to a sealed tube and heated with a microwave condition at 135° C. for 3 h. After cooling, the reaction mixture was diluted in water, extracted with EA. The organic phase was washed with water and brine, dried over Na2SO4, concentrated to afford the title compound (2.10 g) as a brown oil. LCMS: rt=3.25 min, [M+H+]=268

Workup

  1. customtransferred to a sealed tube
  2. temperatureheated with a microwave condition at 135° C. for 3 h
  3. temperatureAfter cooling
  4. extractionextracted with EA
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-27aafc94c9f34c01990a57b21c64ae33
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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