Water → 3'-Methylaminobiphenyl-4-carbaldehyde

HRID 390602Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4](CN)[CH:5]=[CH:6][CH:7]=1.[CH:10]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)=[O:11].O.C(OCC)(=O)C.[CH3:28][N:29](C)C=O>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>[CH3:28][NH:29][C:4]1[CH:5]=[C:6]([C:15]2[CH:16]=[CH:17][C:12]([CH:10]=[O:11])=[CH:13][CH:14]=2)[CH:7]=[CH:2][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

5 g (26.8 mmol) of 3-bromophenylmethylamine and 4 g (26.8 mmol) of commercial 4-formylbenzeneboronic acid are dissolved in 50 mL of an aqueous 6/1 mixture of dimethylformamide/aqueous 2 M potassium phosphate. 1.5 g (1.3 mmol, 5 mol %) of tetrakis(triphenylphosphine)palladium are added. The mixture is stirred for 2 hours at 90° C. The reaction is worked up by addition of 50 mL of water and extraction with ethyl acetate. The organic phases are washed with sodium chloride solution and dried over magnesium sulfate. The solvents are evaporated off, and the residue is then purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 4.3 g (76%) of 3′-methylaminobiphenyl-4-carbaldehyde are obtained.

Workup

washThe organic phases are washed with sodium chloride solution
dry with materialdried over magnesium sulfate
customThe solvents are evaporated off
customthe residue is then purified by chromatography on a column of silica
washeluted with a 7/3 heptane/ethyl acetate mixture

Sources & evidence

ORD record: ord-9393701bfea74b28905c80e7caa59bd1
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383652B2

Reaction notes

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