3-(Trifluoromethoxy)benzaldehyde → HCID 20794915, compound

HRID 1849879Notes

Reaction equation

HRID 1849879 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8].[C:14]1([Mg]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1.CCOC(C)=O>[C:14]1([CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([O:3][C:2]([F:12])([F:13])[F:1])[CH:5]=2)[OH:8])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 6051393-(Trifluoromethoxy)benzaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 20794915HCID 20794915, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(trifluoromethoxy)benzaldehyde (1.30 g, 6.84 mmol) in anhydrous THF (50 mL) was added phenylmagnesium bromide (1.0 M, 17 mL, 17 mmol) dropwise at 0° C. The resulting mixture was stirred at 80° C. for 3 h. The mixture was cooled to room temperature and diluted with EtOAc (100 mL). The organic layer was washed with saturated NH4Cl (50 mL) and brine (50×2 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by reverse phase Combiflash (50%-55% MeCN in 0.5% NH4HCO3) to give target product (1.36 g, 74%) as a pale yellow oil. LCMS (ESI) m/z: 267.1 [M−H]. 1H-NMR (500 MHz, DMSO-d6): δ 7.44-7.40 (m, 5H), 7.33-7.30 (m, 2H), 7.23-7.18 (m, 2H), 6.13 (d, J=4.0 Hz, 1H), 5.79 (d, J=4.0 Hz, 1H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washThe organic layer was washed with saturated NH4Cl (50 mL) and brine (50×2 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by reverse phase Combiflash (50%-55% MeCN in 0.5% NH4HCO3)

Sources & evidence

ORD record
ord-372e2a2864fb4f689f80c8e8a3d54695
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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