Potassium Carbonate → 3-(4-Fluoro-3-(methylsulfonyl)phenyl)-4-methoxybenzaldehyde

HRID 68608

Reaction equation

[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7](B(O)O)[CH:8]=1)=[O:2].Br[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:16]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:7]2[CH:8]=[C:3]([CH:4]=[CH:5][C:6]=2[O:12][CH3:13])[CH:1]=[O:2])=[CH:16][C:17]=1[S:22]([CH3:25])(=[O:23])=[O:24]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 5-Formyl-2-methoxyphenylboronic acid (324 mg, 1.8 mmol, 1.5 eq, Frontier Scientific, Inc., Logan, Utah, USA) in dioxane:H2O (2:1; 15 mL) was added 4-bromo-1-fluoro-2-(methylsulfonyl)benzene (300 mg, 1.2 mmol, 1.0 eq., Apollo Scientific Ltd., Stockport, Cheshire, UK), K2CO3 (496 mg, 3.6 mmol, 2 eq.) and Pd(PPh3)4 (30 mg). The mixture was stirred under nitrogen at 140° C. in a microwave for 40 min. Solvent was evaporated and the residue was dissolved in DCM and washed with water. The DCM layer was dried and evaporated. Purification via column chromatography (eluent: PE:EA=3:1) yielded 400 mg (72%) of 3-(4-fluoro-3-(methylsulfonyl)phenyl)-4-methoxybenzaldehyde (27).

Workup

customSolvent was evaporated
dissolutionthe residue was dissolved in DCM
washwashed with water
dry with materialThe DCM layer was dried
customevaporated
customPurification via column chromatography (eluent: PE:EA=3:1)

Sources & evidence

ORD record: ord-45f4597c36274a5b985838bc77ac4440
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822467B2

Linked notes

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