4-Hydroxybenzaldehyde → 4-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}benzaldehyde

HRID 705963Notes

Reaction equation

HRID 705963 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCOC(C)=O.O>[F:18][C:17]([F:20])([F:19])[C:14]1[CH:15]=[CH:16][C:11]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[N:12][CH:13]=1

Participants

7

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 27364342-Bromo-5-(trifluoromethyl)pyridine

Product 1

HCID 269857004-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}benzaldehydeYield 84.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-hydroxybenzaldehyde (4.094 mmol, 1 eq), 2-bromo-5-(trifluoromethyl)pyridine (4.094 mmol, 1 eq) and potassium carbonate (6.142 mmol, 1.5 eq) were suspended in N,N-dimethylformamide (15 ml). The reaction mixture was irradiated by microwave Biotage Initiator at 130° C. for 30 min. Reaction mixture was diluted with EtOAc (15 ml) and extraction with water followed (3×15 ml). Organic layers were combined, washed with brine, dried over MgSO4, filtered and evaporated giving 4-(5-trifluoromethyl-pyridin-2-yloxy)-benzaldehyde (3.443 mmol, yield=84%, purity=94%). [M+H]+=268.25 1H NMR (300 MHz, DMSO-d6) δ/ppm 7.33-7.38 (m, 1H), 7.43 (d, J=8.5 Hz, 2H), 7.99 (d, J=8.7 Hz, 2H), 8.26-8.33 (m, 1H), 8.57-8.62 (m, 1H)

Workup

  1. customThe reaction mixture was irradiated by microwave Biotage Initiator at 130° C. for 30 min
  2. customReaction mixture
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1f5e7e49ac714e639deaed58b2369f69
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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