Phosphorus oxychloride → HCID 18668990, compound

HRID 1058649Notes

Reaction equation

[Br:1][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.P(Cl)(Cl)(Cl)=O.[C:27]([O-])(=[O:29])C.[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]([C:14]2[CH:15]=[CH:16][C:17]([CH:27]=[O:29])=[CH:18][CH:19]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In an argon atmosphere, N-(4-bromobenzyl)diphenylamine (169 mg, 0.500 mmol) obtained in Example 64 was dissolved in dimethylformamide (1.5 mL), and phosphorus oxychloride (0.116 mL, 1.25 mmol) was added thereto, followed by stirring at 100° C. for 30 minutes. The reaction liquid was cooled to room temperature, poured into saturated sodium acetate aqueous solution, and 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 (elution solvent:hexane/ethyl acetate=4/1) to give 4-[N-(4-bromobenzyl)-N-phenylamino]-benzaldehyde (159 mg, 87%).

Workup

customThe reaction liquid
temperaturewas cooled to room temperature
extractionwas 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 (elution solvent:hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-11cc65af686e4ea2a1646f2d485fd8b7
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518268B1

Reaction notes

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