Water → 4-(N,N-diphenylaminomethyl)benzaldehyde

HRID 1058645Notes

Reaction equation

Br[C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.CN(C)[CH:35]=[O:36].O>O1CCCC1>[C:8]1([N:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:2]([CH:35]=[O:36])=[CH:3][CH:4]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In an argon atmosphere, the thus obtained N-(4-bromobenzyl)diphenylamine (440 mg, 1.30 mmol) was dissolved in tetrahydrofuran (6 mL) and cooled to −78° C. A 1.6 M n-butyl lithium hexane solution (1.3 mL, 2.0 mmol) was added thereto, and, 5 minutes thereafter, dimethylformamide (0.20 mL, 2.6 mmol) was further added thereto, followed by stirring for 5 minutes. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (9:1 hexane/ethyl acetate) to obtain 4-(N,N-diphenylaminomethyl)benzaldehyde (213 mg, 57%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (9:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-6934cce5d46f4c62a944070c294d87b8
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518268B1

Reaction notes

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