Dimethylformamide → 2-(2,5-Difluorophenylthio)-5-methoxy-benzaldehyde

HRID 1388537Notes

Reaction equation

HRID 1388537 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[F:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[SH:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>[Cu].O>[F:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[S:20][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3444802-Bromo-5-methoxybenzaldehydeHCID 38363232,5-Difluorobenzene-1-thiol

Product 1

HCID 128159522-(2,5-Difluorophenylthio)-5-methoxy-benzaldehydeYield 52%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 19.7 g of 2-bromo-5-methoxybenzaldehyde (of Example 9, reference above), 14.1 g of 2,5-difluorothiophenol (of Example 11, reference above), 14.0 g of potassium carbonate, 75 ml dimethylformamide and 2.1 g of copper catalyst is stirred and heated to 150° C. for 6 hours. It is then diluted with 150 ml of water and extracted with benzene. The extract is washed with water, dried with magnesium sulfate and evaporated. The residue is processed by distillation. There are obtained 13.3 g (52%) of 2-(2,5-difluorophenylthio)-5-methoxy-benzaldehyde boiling at 163°-165° C./40 Pa. The product is crystallized from cyclohexane and melts in a pure state at 67°-68° C.

Workup

  1. extractionextracted with benzene
  2. washThe extract is washed with water
  3. dry with materialdried with magnesium sulfate
  4. customevaporated
  5. distillationThe residue is processed by distillation

Sources & evidence

ORD record
ord-0f3fefc692ba4cd192befc23e910e4a9
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

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