4-Fluorophenol → HCID 58753821, compound

HRID 1484176Notes

Reaction equation

HRID 1484176 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C.O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:2]2[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 58753821HCID 58753821, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-fluoro-4-(trifluoromethyl)benzaldehyde (1.0 g, 5.20 mmol) and 4-fluorophenol (583.5 mg, 5.20 mmol) in DMF (5.0 mL) was added dicesium carbonate (1.7 g, 5.20 mmol) and the mixture was heated at 100° C. for 1 hour. The reaction was cooled to room temperature. The reaction was diluted with ethyl acetate (5 ml) and water (10 ml). The organic layer was washed with water (2×10 mL), dried with MgSO4, filtered and evaporated to yield a brown oil that was purified by column chromatography using a gradient of ethyl acetate in hexanes (0-25%) to yield 2-(4-fluorophenoxy)-4-(trifluoromethyl)benzaldehyde (1.16 g, 78%). 1H NMR (400 MHz, CDCl3) δ 10.58 (s, 1H), 8.04 (d, J=8.0 Hz, 1H), 7.42 (d, J=7.5 Hz, 1H), 7.18-7.04 (m, 5H) ppm.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washThe organic layer was washed with water (2×10 mL)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto yield a brown oil that
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1169288d6a37482e9d4a573768b5d630
Source dataset
uspto-grants-2016_08
Patent number
US09421196B2

Reaction notes

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