2-Chlorobenzaldehyde → HCID 818029, compound

HRID 1388530Notes

Reaction equation

HRID 1388530 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[OH-].[Na+].Cl[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15]>CN(C)P(N(C)C)(N(C)C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15]

Participants

6

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 5202162-Fluorothiophenol

Product 1

HCID 818029HCID 818029, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 43.8 g 2-fluorothiophenol (I. Cervena et al., Collect. Czech. Chem. Commun. 44, 2139, 1979) in 85 ml of hexamethylphosphoramide is treated in a nitrogen atmosphere first with a solution of 13.6 g sodium hydroxide in 26 ml of water and then with 45.0 g of 2-chlorobenzaldehyde. Then the mixture is heated for 3.5 hours to 100° C. It is next poured into 500 ml of water and the product extracted with benzene. The extract is dried with magnesium sulfate and evaporated. The residue crystallizes after mixing with 120 ml of petroleum ether. There are obtained 57.1 g (77%) 2-(2-fluorophenylthio)benzaldehyde, crystallizing from benzene and melting in pure state at 56°-57° C.

Workup

  1. temperatureThen the mixture is heated for 3.5 hours to 100° C
  2. extractionthe product extracted with benzene
  3. dry with materialThe extract is dried with magnesium sulfate
  4. customevaporated
  5. customThe residue crystallizes
  6. additionafter mixing with 120 ml of petroleum ether

Sources & evidence

ORD record
ord-5bc8d6804ec34ad5a47772d64d4077df
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

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