Phenol → HCID 66882266, compound

HRID 1820698Notes

Reaction equation

[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:12]=1[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>[Cu]Br.CCCCCCC.C(Cl)Cl>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][O:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([O:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:12]=2[CH3:27])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 180 °C

Procedure

Sodium hydride as a 60% dispersion in mineral oil (56 mg, 1.4 mmol) was added portionwise to a solution of phenol (0.35M in DMF, 2 mL). The resultant solution was added to a mixture of 1-bromo-3-(4-methoxybenzyloxy)-2-methylbenzene (215 mg, 0.7 mmol) and cesium carbonate (228 mg, 0.7 mmol) in a microwave vessel. Copper (I) bromide (10 mg) was added, the vessel was sealed and the reaction heated at 180° C. for 900 s. 1N NaOH (aq) (2 mL) and DCM (5 mL) were added to the cooled reaction mixture and the organic layer was separated and concentrated in vacuo. The crude material was then purified by chromatography on silica gel. Elution with 5:95 ethyl acetate:heptane afforded 1-(4-methoxybenzyloxy)-2-methyl-3-phenoxybenzene (205 mg, 0.64 mmol, 91%).

Workup

customthe vessel was sealed
customthe organic layer was separated
concentrationconcentrated in vacuo
customThe crude material was then purified by chromatography on silica gel
washElution with 5:95 ethyl acetate

Sources & evidence

ORD record: ord-e162819c4bf640a8b6bbbf59a942cb6d
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605170B2

Reaction notes

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