Potassium Carbonate → 4-(4-Bromo-2-fluoro-phenoxy)-2,6-dimethyl-pyridine

HRID 404705Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:18])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=2)=[C:13]([F:18])[CH:12]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-bromo-2,6-dimethyl-pyridine (1 g, 5.4 mmol), 4-bromo-2-fluoro-phenol (0.59 g, 5.4 mmol) and potassium carbonate (0.89 g, 6.4 mmol) in xylenes (2 ml) was heated at 150° C. (oil bath temperature) into a sealed tube for 48 hours. After cooling to room temperature the mixture was diluted with EtOAc and filtered through a diatomaceous earth pad. The filtrate was evaporated till dryness and the crude product thus obtained was purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 10% as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate D22 (1.28 g, 80%).

Workup

temperatureAfter cooling to room temperature the mixture
filtrationfiltered through a diatomaceous earth pad
customThe filtrate was evaporated till dryness

Sources & evidence

ORD record: ord-a9c14be0b953419eb4bac2265fc2e087
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748621B2

Reaction notes

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