Potassium Carbonate → HCID 86624482, compound

HRID 1667645Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[F:11][C:12]([F:22])([F:21])[O:13][C:14]1[CH:19]=[CH:18][C:17](O)=[CH:16][CH:15]=1.C(=O)([O-])[O-:24].[K+].[K+]>[Cu]=O.N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]([F:22])([F:21])[F:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 5-bromo-2-fluorobenzaldehyde (1.07 g, 5.280 mmol), 4-(trifluoromethoxy)phenol (940 mg, 5.280 mmol), potassium carbonate (1.46 g, 10.560 mmol), copper(II) oxide (420 mg, 5.280 mmol) and pyridine (10 ml) was stirred at 180° C. for 6 hours. The reaction mixture was cooled to room temperature and filtered through celite. The filtrate was diluted with water, extracted with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=6:1) to give the title compound (1.58 g, 83.1%) as a brown oil.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through celite
additionThe filtrate was diluted with water
extractionextracted with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe residue obtained by evaporation of the solvent under reduced pressure
customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record: ord-387cccae1f704dedbfb7d85d9d4e3aab
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044236B2

Reaction notes

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