Potassium Hydroxide → HCID 12374919, compound

HRID 1732777Notes

Reaction equation

HRID 1732777 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][C:3]=1[O:9][CH3:10].Br[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[CH2:19][C:20]([OH:22])=[O:21].[OH-].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:14]2[CH:15]=[C:16]([F:18])[CH:17]=[CH:12][C:13]=2[CH2:19][C:20]([OH:22])=[O:21])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 34778092-Bromo-4-fluorophenylacetic acidHCID 123746014-Chloro-3-methoxybenzene-1-thiol

Product 1

HCID 12374919HCID 12374919, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-3-methoxythiophenol (see Example 30) (36.2 g), 2-bromo-4-fluorophenylacetic acid (see the preceding Example) (39.6 g), potassium hydroxide (20 g) and dimethylformamide (250 ml) is heated to 100° C. while stirring until formation of a homogeneous solution. The greatest part of the dimethylformamide is distilled off under normal pressure, removing also the water arising by neutralization. Dimethylformamide (250 ml), anhydrous potassium carbonate (10 g) and copper (6 g) are added to the residue and the mixture is stirred for 14 hours in a bath heated to 170° C. The solvent is evaporated in vacuo, the residue dissolved in water, filtered and the filtrate made acidic by addition of hydrochloric acid. The separated oily acid is extracted with a large volume of warm benzene. The extract is then worked up, yielding 40 g of the crude 2-(4-chloro-3-methoxyphenylthio)-4-fluorophenylacetic acid which is crystallized from aqueous ethanol or cyclohexane. The pure compound melts at 118°-119° C.

Workup

  1. distillationThe greatest part of the dimethylformamide is distilled off under normal pressure
  2. customremoving also the water arising by neutralization
  3. additionDimethylformamide (250 ml), anhydrous potassium carbonate (10 g) and copper (6 g) are added to the residue
  4. stirringthe mixture is stirred for 14 hours in a bath
  5. temperatureheated to 170° C
  6. customThe solvent is evaporated in vacuo
  7. dissolutionthe residue dissolved in water
  8. filtrationfiltered
  9. additionthe filtrate made acidic by addition of hydrochloric acid
  10. extractionThe separated oily acid is extracted with a large volume of warm benzene

Sources & evidence

ORD record
ord-4fc7f554a34a47d6b650f7957deebf1a
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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