Diglyme → 4'-Fluoro(1,1'-biphenyl)-2-amine

HRID 1663240Notes

Reaction equation

Br[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].COCCOCCOC.C(=O)([O-])[O-].[Na+].[Na+].[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.B(O)O>C(O)C.C(OCC)(=O)C>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[NH2:4])=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2-bromoaniline (1.72 g, 10.0 mmol) in diglyme (30 mL) tetrakis(triphenylphosphine)-palladium(0) (0.13 g, 0.3 mmol) and 2.0 M aqueous sodium carbonate solution (15 mL, 30.0 mmol) were added. In a separate flask, 4-fluorophenylboronic acid (2.23 g 16.0 mmol) was dissolved in ethanol (8 mL) and the mixture containing 2-bromoaniline was added to this boronic acid solution. The obtained brown reaction mixture was heated at 80° C. for 6 hours, then cooled, diluted with ethyl acetate and washed with saturated ammonium chloride solution. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography using Kieselgel 60 (0.015-0.040 mm) as adsorbent (Merck) and n-hexane:ethyl-acetate=2:1 as eluent to yield after recrystallization from ethanol 1.8 g (60%) of the title compound as white crystals.

Workup

temperaturecooled
washwashed with saturated ammonium chloride solution
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash column chromatography
customethyl-acetate=2:1 as eluent to yield
customafter recrystallization from ethanol 1.8 g (60%) of the title compound as white crystals

Sources & evidence

ORD record: ord-bde24fca292d47739a7e6cad5611ac38
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034827B2

Reaction notes

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