Dimethylformamide → 2-[(3-Chlorophenyl)thio]-5-methoxybenzoic acid

HRID 1377790Notes

Reaction equation

HRID 1377790 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].Br[C:21]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24]>O>[Cl:1][C:2]1[CH:3]=[C:4]([S:8][C:21]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:22]=2[C:23]([OH:25])=[O:24])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 162573-ChlorothiophenolHCID 899062-Bromo-5-methoxybenzoic acid

Product 1

HCID 3411532-[(3-Chlorophenyl)thio]-5-methoxybenzoic acidYield 60.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 3-chlorothiophenol (20 g, 138 mol), and cupric acetate (1.8 g) and DMF (200 mL) was added K2CO3 (23 g). The mixture was heated to 150° C. for 15-20 minutes, then 2-bromo-5-methoxybenzoic acid (35.8 g, 0.155 mol) was added in portions. The mixture was heated overnight, poured into water (600 mL), filtered and the filtrate was treated with charcoal, filtered and diluted with HCl. The resulting precipitate was collected by filtration, washed with water, and dried at 50° C. in vacuo over P2O5 to afford 27.6 g of 2-[(3-chlorophenyl)thio]-5-methoxybenzoic acid.

Workup

  1. temperatureThe mixture was heated overnight
  2. filtrationfiltered
  3. additionthe filtrate was treated with charcoal
  4. filtrationfiltered
  5. additiondiluted with HCl
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. dry with materialdried at 50° C. in vacuo over P2O5

Sources & evidence

ORD record
ord-98b358748542462683cb693f06d3c324
Source dataset
uspto-grants-1997_09
Patent number
US05665760

Reaction notes

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