Sodium Carbonate → 2,4-Dimethyl-6-(2-thienyl)phenol

HRID 63381

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([C:12]2[S:11][CH:15]=[CH:14][CH:13]=2)[C:3]=1[OH:10]

Participants

Conditions

Temperature: 120 °C

Procedure

2-Bromo-4,6-dimethylphenol (500 mg, 2.49 mmol), 2-thiophenyl boronic acid (88 mg, 2.99 mmol), sodium carbonate (791 mg, 7.47 mmol) and Pd2(dppf)2Cl2 (406 mg, 0.49 mmol) were dissolved in dimethoxyethane/water 6 mL/3 mL, followed by stirring in microwave at 120° C. for 20 minutes. After the completion of the reaction, the reaction mixture was filtered using Celite. The filtrate was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by column chromatography (ethyl acetate:hexane=1:3) to obtain 2,4-dimethyl-6-(thiophene-2-yl)phenol (231 mg, 45%).

Workup

customAfter the completion of the reaction
filtrationthe reaction mixture was filtered
additionThe filtrate was added with water
extractionextracted with ethyl acetate
dry with materialThe obtained organic layer was dried over magnesium sulfate
custompurified by column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record: ord-d42cca8043834a089eaabd02a21e9477
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447083B2

Linked notes

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