Water → 4'-Tert-butyl-2,5-dimethylbiphenyl-4-amine

HRID 1673189Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:15]1[C:21]([CH3:22])=[CH:20][C:18]([NH2:19])=[C:17]([CH3:23])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>COCCOC.C1CCCCC1.C(OC(=O)C)C.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[CH:16]=[C:17]([CH3:23])[C:18]([NH2:19])=[CH:20][C:21]=2[CH3:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

The reaction is carried out using inert conditions (argon or nitrogen atmosphere, dry solvents). A suspension of 6.4 g (36.0 mmol) of (4-tert-butylphenyl)boronic acid, 6.0 g (30.0 mmol) of 4-bromo-2,5-dimethylaniline, 29.3 g (90 mmol) caesium carbonate and 0.7 g (0.6 mmol) tetrakis(triphenylphosphin)palladium in 75 ml of 1,2-dimethoxyethan was stirred for 16 hrs at 80° C. At room temperature 25 ml of water and 75 ml of toluene were added. The organic layer was separated, the watery layer was again extracted using 75 ml of toluene. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Column chromatographic (cyclohexane/ethylacetate:2/1) yielded 5.5 g (21.7 mmol) 72% of 4′-tert-butyl-2,5-dimethylbiphenyl-4-amine (log P (pH 2.3)=3.65.

Workup

customThe organic layer was separated
extractionthe watery layer was again extracted
dry with materialThe combined organic layers were dried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a785811753f444e9903adc4db75da154
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999137B2

Reaction notes

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