Potassium Carbonate → 4-(3,4-Difluorophenoxy)benzaldehyde

HRID 2087406Notes

Reaction equation

HRID 2087406 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][C:11]1[CH:12]=[C:13]([OH:18])[CH:14]=[CH:15][C:16]=1[F:17].C([O-])([O-])=O.[K+].[K+]>>[F:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][C:16]=1[F:17])[O:18][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 759273,4-Difluorophenol

Product 1

HCID 105857414-(3,4-Difluorophenoxy)benzaldehyde

Procedure

4-Fluorobenzaldehyde (5.32 mL, 49.6 mmol), 3,4-difluorophenol (7.10 g, 54.6 mmol) and K2CO3 (8.31 g, 60.1 mmol) were combined in a flask, which was immediately flushed with argon. DMF (50.0 mL) was added and the mixture was heated at ref lux under argon for 6 h. Upon cooling to room temperature, EtOAc (100 mL) and H2O (100 mL) were added; the ethyl acetate layer was separated and washed with H2O (2×100 mL). The combined organic layers were washed with brine, dried over MgSO4, and the solvent was removed in vacuo. The desired product was obtained (11.4 g, 98.0%): 1H NMR (400 MHz, CDCl3) δ 9.95 (s, 1H), 7.88 (dd, 2H, J=0.8 Hz, 8.8 Hz), 7.24-7.17 (m, 1H), 7.07 (d, 2H, J=8.8 Hz), 6.97-6.92 (m, 1H), 6.86-6.82 (m, 1H); ESMS m/e: 235.0 (M+H)+.

Workup

  1. customwhich was immediately flushed with argon
  2. additionDMF (50.0 mL) was added
  3. temperaturethe mixture was heated at ref lux under argon for 6 h
  4. additionEtOAc (100 mL) and H2O (100 mL) were added
  5. customthe ethyl acetate layer was separated
  6. washwashed with H2O (2×100 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8ddbf4d42111411bb6147082e17010b7
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

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