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

HRID 1058653Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A 2.5 mol/L sodium hydroxide aqueous solution (1.7 mL, 4.4 mmol) and tetrabutylammonium bromide (0.017 g, 0.051 mmol) were added to 2-chlorobenzenethiol (0.17 g, 1.0 mmol), followed by stirring at 25° C. for 10 minutes. To the reaction liquid was added a toluene (1.7 mL) solution of 2-fluoro-5-nitrobenzaldehyde (0.18 g, 1.0 mmol), followed by stirring at 110° C. for 2 hours. After the conventional post-reaction treatment, the residue was purified by silica gel chromatography (eluted by chloroform) to give 2-[(2-chlorophenyl)thio]-5-nitrobenzaldehyde (0.25 g, 83%).

Workup

customTo the reaction liquid
stirringby stirring at 110° C. for 2 hours
customAfter the conventional post-reaction treatment, the residue was purified by silica gel chromatography (eluted by chloroform)

Sources & evidence

ORD record: ord-b1d3b367fdf04450b920786fa93d2ed6
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518268B1

Reaction notes

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