Potassium Carbonate → Methyl 2'-methyl-2-nitro-1,1'-biphenyl-4-carboxylate

HRID 336236

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[CH3:24][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of methyl 4-bromo-3-nitrobenzoate (Chess 1687; 3 g; 11.53 mmol; 1 eq.), o-tolylboronic acid (Aldrich 393606; 1.88 g; 13.84 mmol; 1.2 eq.), potassium carbonate (7.97 g, 57.68 mmol, 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (668.2 mg, 0.577 mmol, 0.05 eq.) in toluene (15 mL) and water (15 mL) was stirred at 120° C. for 14 hours. The resulting mixture was allowed to return to room temperature and the two phases were separated. The organic layer was concentrated in vacuo and purified by column chromatography (c-hexane) to afford the title compound (2.5 g, 79%) as a white solid.

Workup

customto return to room temperature
customthe two phases were separated
concentrationThe organic layer was concentrated in vacuo
custompurified by column chromatography (c-hexane)

Sources & evidence

ORD record: ord-4622f46388114386990033ed569a94cf
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889668B2

Linked notes

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