Sodium Hydroxide → 2-[(3-Chlorophenyl)thio]-5-nitrobenzaldehyde

HRID 1058652Notes

Reaction equation

[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([SH:10])[CH:7]=[CH:8][CH:9]=1.F[C:12]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=1[CH:14]=[O:15]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:5]=[C:6]([S:10][C:12]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=2[CH:14]=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A 2.5 mol/L sodium hydroxide aqueous solution (1.2 mL, 3.1 mmol) and tetrabutylammonium bromide (0.012 g, 0.031 mmol) were added to 3-chlorobenzenethiol (0.11 g, 0.73 mmol), followed by stirring at 25° C. for 10 minutes. A toluene (1.2 mL) solution of 2-fluoro-5-nitrobenzaldehyde (0.12 g, 0.73 mmol) was added to the reaction liquid, followed by stirring at 110° C. for 1.5 hours. After the conventional post-reaction treatment, the residue was purified by silica gel chromatography (eluted by chloroform) to give 2-[(3-chlorophenyl)thio]-5-nitrobenzaldehyde (72 mg, 34%).

Workup

stirringby stirring at 110° C. for 1.5 hours
customAfter the conventional post-reaction treatment, the residue was purified by silica gel chromatography (eluted by chloroform)

Sources & evidence

ORD record: ord-45aa067acfe04d47854a433f8fb0f143
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518268B1

Reaction notes

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