Water → 4-(Dibenzylamino)benzaldehyde

HRID 1058647Notes

Reaction equation

Br[C:2]1[CH:22]=[CH:21][C:5]([N:6]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:7][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:36]=[O:37].O>O1CCCC1>[CH2:7]([N:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:5]1[CH:21]=[CH:22][C:2]([CH:36]=[O:37])=[CH:3][CH:4]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In an argon atmosphere, the obtained 4-bromo-N,N-dibenzylaniline (425 mg, 1.21 mmol) was dissolved in tetrahydrofuran (5 mL) and cooled to −78° C. A 1.6 M n-butyl lithium hexane solution (1.1 mL, 1.8 mmol) was added thereto, and, 5 minutes thereafter, dimethylformamide (0.186 mL, 2.4 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 a saturated 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-(dibenzylamino)benzaldehyde (192 mg, 53%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with a saturated 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-1903227c4a5744f886a98ae7ef0c5223
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518268B1

Reaction notes

Loading…