Water → HCID 58748417, compound

HRID 2424389Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([N+:26]([O-:28])=[O:27])[CH:20]=1.O>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([N+:26]([O-:28])=[O:27])[CH:20]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-methoxyphenyl-boronic acid (500 mg, 3.29 mmol) in toluene (5.2 mL) and ethanol (1.3 mL), potassium carbonate (910 mg, 6.58 mmol), tetrakis(triphenylphosphine)-palladium (228.1 mg, 0.099 mmol) and 4-bromo-1-methyl-2-nitrobenzene (711 mg, 3.29 mmol) are added and stirred at 100° C. for 7 hours. The mixture is poured into water and extracted with ethyl acetate two times. The organic layer is washed with water and then brine, dried over magnesium sulfate, and evaporated in vacuo. The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1) to afford the 4′-methoxy-4-methyl-3-nitro-biphenyl (630 mg, 79%) as a yellow solid.

Workup

extractionextracted with ethyl acetate two times
washThe organic layer is washed with water
dry with materialbrine, dried over magnesium sulfate
customevaporated in vacuo
customThe residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-dfa1167b576049c0bbf49f366d4fed84
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964592B2

Reaction notes

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