p-Bromobenzenesulfonyl chloride → HCID 13321572, compound

HRID 1262818Notes

Reaction equation

HRID 1262818 reaction equation
[CH3:1][C:2]1[C:6]([OH:7])=[C:5]([C:8]([O:10][CH2:11][CH2:12][CH3:13])=[O:9])[S:4][C:3]=1[C:14]([O:16][CH2:17][CH2:18][CH3:19])=[O:15].O1CCOCC1.C(=O)([O-])[O-].[K+].[K+].[Br:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>CC(C)=O>[CH3:1][C:2]1[C:6]([O:7][S:39]([C:36]2[CH:37]=[CH:38][C:33]([Br:32])=[CH:34][CH:35]=2)(=[O:41])=[O:40])=[C:5]([C:8]([O:10][CH2:11][CH2:12][CH3:13])=[O:9])[S:4][C:3]=1[C:14]([O:16][CH2:17][CH2:18][CH3:19])=[O:15]

Participants

6

Reactant 4

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 54732940Dipropyl 3-hydroxy-4-methylthiophene-2,5-dicarboxylate

Product 1

HCID 13321572HCID 13321572, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.3 g (8 mmol) of dipropyl 3-methyl-4-hydroxy-2,5-thiophene-dicarboxylate, 20 ml of dioxane, 40 ml of acetone, 1.6 g (12 mmol) of anhydrous potassium carbonate and 2.3 g (10 mmol) of 4-bromobenzene-sulfonyl chloride was refluxed for about 10 hours, removed of dioxane and acetone by distillation, added with ethyl ether, washed with water, and dried with anhydrous magnessium sulfate. The solvent was removed by distillation, and recrystallization was effected with use of methanol to give 3.8 g (94%) of the desired white crystalline compound, m.p. 73°-74° C.

Workup

  1. temperaturewas refluxed for about 10 hours
  2. customremoved of dioxane and acetone by distillation
  3. additionadded with ethyl ether
  4. washwashed with water
  5. dry with materialdried with anhydrous magnessium sulfate
  6. customThe solvent was removed by distillation, and recrystallization
  7. customto give 3.8 g (94%) of the desired white crystalline compound, m.p. 73°-74° C.

Sources & evidence

ORD record
ord-1420cc2c129a4a4ab1db2cfae5bd0a81
Source dataset
uspto-grants-1984_06
Patent number
US04454131

Reaction notes

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