Potassium Phosphate, Tribasic → 5-Cyclopropyl-1,3-difluoro-2-nitrobenzene

HRID 447775

Reaction equation

Br[C:2]1[CH:3]=[C:4]([F:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1.[CH:13]1(B(O)O)[CH2:15][CH2:14]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[Na+].[Br-]>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.C1(C)C=CC=CC=1>[CH:13]1([C:2]2[CH:3]=[C:4]([F:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=2)[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 160 °C

Procedure

5-bromo-1,3-difluoro-2-nitrobenzene (D24, 560 mg, 2.35 mmol), cyclopropylboronic acid (1 eq., 2.35 mmol, 0.2 g), K3PO4 (3 eq., 7.1 mmol, 1.50 g), NaBr (1 eq., 2.35 mmol, 0.24 g) and Pd(PPh3)4 (280 mg) were added to 3 ml of dry toluene and the mixture was heated by microwave at 160° C. for 40 minutes. The mixture was then poured onto water (10 ml) and extracted with ethyl acetate (3×20 ml). The combined organics were dried over MgSO4, filtered and the solvent was evaporated to afford 660 mg of brown crude product which was purified by silica gel chromatography (5-20% diethyl ether-40-60° petroleum ether) to afford the title compound as a yellow oil, 300 mg, 64%.

Workup

additionThe mixture was then poured onto water (10 ml)
extractionextracted with ethyl acetate (3×20 ml)
dry with materialThe combined organics were dried over MgSO4
filtrationfiltered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-562985611e7a4cdeaa8c4734b214ebe1
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481566B2

Linked notes

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