Potassium Carbonate → (5'-Methyl-2',4'-dinitro-biphenyl-4-yl)-methanol

HRID 1773535Notes

Reaction equation

Cl[C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[OH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([CH2:16][OH:15])=[CH:18][CH:19]=2)[CH:7]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 5-chloro-2,4-dinitrotoluene (1.0 g), 4-(hydroxymethyl)phenylboronic acid (0.84 g), bis(triphenylphosphine)palladium(II) chloride (150 mg) and potassium carbonate (2.0 g) in a mixture of 1,4-dioxane and water (10/1, 11 mL) was heated at 170° C. in a microwave reactor for 10 minutes. The reaction mixture was then cooled and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (acetone/DCM, 3/97) to give 0.6 g of (5′-methyl-2′,4′-dinitro-biphenyl-4-yl)-methanol.

Workup

temperatureThe reaction mixture was then cooled
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe crude residue was purified by flash chromatography (acetone/DCM, 3/97)

Sources & evidence

ORD record: ord-cac1e69d2e6d478fa25e9bd30bd6bc46
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255110B2

Reaction notes

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