Methanethiol → 5'-Fluoro-2'-Formyl-4-Methylthiobiphenyl

HRID 376443Notes

Reaction equation

HRID 376443 reaction equation
[OH-].[K+].[CH3:3][SH:4].O.Cl[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[CH:20]=[O:21])=[CH:9][CH:8]=1>C(O)C>[F:19][C:17]1[CH:16]=[CH:15][C:14]([CH:20]=[O:21])=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([S:4][CH3:3])=[CH:8][CH:9]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 878Methanethiol2×HCID 962Water2×HCID 14797Potassium HydroxideHCID 193619434'-Chloro-5-fluoro-[1,1'-biphenyl]-2-carbaldehyde

Product 1

HCID 193619465'-Fluoro-2'-Formyl-4-Methylthiobiphenyl

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

85% potassium hydroxide solution (66 g) is dissolved in ethanol (700 ml) and cooled to room temperature. To this with stirring is added methyl mercaptan subsurface (50 g), water (2ml) and a solution of 4-chloro-5'-fluoro-2'-formylbiphenyl (234.5 g) in ethanol (300 ml). A slow stream of methyl mercaptan is continuously fed in while the reaction mixture is held at reflux for 3 hours. The reaction is poured into water (1 liter), and the solid is filtered off. The solid is recrystallized from benzene.

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationthe solid is filtered off
  3. customThe solid is recrystallized from benzene

Sources & evidence

ORD record
ord-4aae6ecab7d04d8499cbb449b5ad94c5
Source dataset
uspto-grants-2000_02
Patent number
US06020379

Reaction notes

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