Sodium Hydroxide → HCID 18668930, compound

HRID 1058663Notes

Reaction equation

[OH-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1)[CH3:4].F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=2[N+:21]([O-:23])=[O:22])=[CH:7][CH:6]=1)[CH3:4]

Participants

Conditions

Temperature: 25 °C

Procedure

A 2.5 mol/L sodium hydroxide aqueous solution (2.0 mL, 4.9 mmol), and tetrabutylammonium bromide (0.019 g, 0.58 mmol) were added to 4-ethylbenzenethiol (0.20 g, 1.2 mmol), followed by stirring at 25° C. for 5 minutes. A toluene solution (2.0 mL) of 4-fluoro-3-nitrobenzaldehyde (0.20 g, 1.2 mmol) was added to the reaction liquid, followed by stirring at 25° C. for 12 hours. After the conventional post-reaction treatment, the product was purified by silica gel column chromatography (eluted by chloroform) to give 4-[(4-ethylphenyl)thio]-3-nitrobenzaldehyde (0.25 g, 75%).

Workup

stirringby stirring at 25° C. for 12 hours
customAfter the conventional post-reaction treatment, the product was purified by silica gel column chromatography (eluted by chloroform)

Sources & evidence

ORD record: ord-14f0376720704986a482b3cda4c00f84
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518268B1

Reaction notes

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