Water → HCID 58748417, compound

HRID 2382654Notes

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-nitrobiphenyl (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-d252985a4c3e4e6180bb69a3bf0b3581
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263590B2

Reaction notes

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