Water → HCID 57687750, compound

HRID 2040918Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[F:11].Br[C:13]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:14]=1[NH2:15].O>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:14]=2[NH2:15])=[CH:4][C:3]=1[F:11]

Participants

Conditions

Temperature: 80 °C

Procedure

Under protective gas atmosphere, a mixture consisting of 30.0 g (0.17 mol) of 4-chloro-3-fluorophenylboronic acid and 29.7 g (0.16 mol) of 2-bromo-4-fluoroaniline in 170 ml of toluene and 17 ml of ethanol is treated with 3.6 g (0.003 mol) of tetrakis(triphenylphosphine)palladium(0) and stirred for 16 h at 80° C. After addition of 200 ml of toluene and 200 ml of water, the organic phase is separated off, dried over magnesium sulphate and concentrated in vacuum. Column chromatography (petroleum ether/acetone 4:1) yields 26.1 g (70% of theory) of 4′-chloro-5,3′-difluorobiphenyl-2-yl-amine with a logP (pH 2.3) of 3.18.

Workup

customthe organic phase is separated off
dry with materialdried over magnesium sulphate
concentrationconcentrated in vacuum

Sources & evidence

ORD record: ord-29ba3e55ee81464ca7879e1c4ad77e13
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580971B2

Reaction notes

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