Potassium Carbonate → 4-Bromo-1-[(4-methoxybenzyl)oxy]-2-(trifluoromethyl)benzene

HRID 522256Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=1.CN1CCCC1=O>O>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[C:20]([C:25]([F:26])([F:27])[F:28])[CH:19]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Potassium carbonate (25.8 g) and 1-(chloromethyl)-4-methoxybenzene (14.4 mL) were added to a mixture of 4-bromo-2-(trifluoromethyl)phenol (15 g) and N-methyl pyrrolidone (100 mL) at room temperature, and the mixture was stirred at 90° C. for 3 hours. After the reaction mixture was cooled to room temperature, water was added thereto, then extraction thereof was performed using EtOAc, and the extract was washed with water. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=9:1 to 6:1), whereby 4-bromo-1-[(4-methoxybenzyl)oxy]-2-(trifluoromethyl)benzene (22 g) was obtained as a colorless oil.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
extractionextraction
washthe extract was washed with water
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (Hex:EtOAc=9:1 to 6:1)

Sources & evidence

ORD record: ord-6d7357d801914936ade60792f7ba8704
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328118B2

Reaction notes

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