Sodium Carbonate → HCID 54912257, compound

HRID 2206852Notes

Reaction equation

[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:3]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[C:5]([NH2:6])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Under argon, a mixture of 9.0 g (37.9 mmol) of 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 10.25 g (45.5 mmol) of 4-bromobenzotrifluoride, 1.39 g (1.89 mmol) of 1,1′-bis(diphenyl-phosphino)ferrocenepalladium(II) chloride and 20.11 g (189 mmol) of sodium carbonate in 200 mL of DMSO and 70 mL of water is stirred at 90° C. overnight. After the reaction has ended, the mixture is cooled to room temperature, water is added and the mixture is extracted with ethyl acetate. The organic phase is once more washed with water, dried with sodium sulfate and concentrated under reduced pressure. The crude product is purified by column chromatography (mobile phase: cyclohexane/ethyl acetate gradient). This gives 5.28 g (53% of theory) of 5-fluoro-4′-(trifluoromethyl)biphenyl-2-amine having a content of 97% according to LC-MS and a logP (acidic) of 3.52.

Workup

temperaturethe mixture is cooled to room temperature
extractionthe mixture is extracted with ethyl acetate
washThe organic phase is once more washed with water
dry with materialdried with sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude product is purified by column chromatography (mobile phase: cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record: ord-ef835d7f76894537b73e6bf1ea6026fd
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375004B2

Reaction notes

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