Dimethylformamide → HCID 22915307, compound

HRID 1769189Notes

Reaction equation

HRID 1769189 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]([Br:30])=[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]([Br:30])=[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 118912,5-Dibromobenzoic acidHCID 162573-Chlorothiophenol

Product 1

HCID 22915307HCID 22915307, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 3-chlorothiophenol (20 g, 0.138 mol), cupric acetate (1.75 g) and DMF (199 mL) under N2 was added in portions K2CO3 (23 g). The mixture was heated to 150° C. and then 2,5-dibromobenzoic acid (43.5 g) was added. The mixture was heated overnight, poured into water (600 mL), filtered, the filtrate was treated with charcoal and filtered again. The filtrate was acidified with conc. HCl, extracted with CHCl3, the organic layer was washed with brine and dried over Na2SO4. The solvent was removed in vacuo to afford 28.9 g of 2-[(3-chlorophenyl)thio]-5-bromobenzoic acid.

Workup

  1. temperatureThe mixture was heated overnight
  2. filtrationfiltered
  3. additionthe filtrate was treated with charcoal
  4. filtrationfiltered again
  5. extractionextracted with CHCl3
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5de4e388dfa74069b041b0697e513f32
Source dataset
uspto-grants-1995_01
Patent number
US05380749

Reaction notes

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