Acetic Acid → 219945-37-6

HRID 428573Notes

Reaction equation

HRID 428573 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[CH3:12][CH:13]([OH:15])[CH3:14].N1C=CC=CC=1.C(O)(=O)C>C(OC)(C)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O:15][CH:13]([CH3:14])[CH3:12])(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 3776IsopropanolHCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 10684044219945-37-6

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

2-Bromobenzenesulfonyl chloride (50 g, 0.19 mol) was suspended in 2-propanol (45 mL, 3 equiv.) and the slurry was cooled to less than 10° C. Pyridine (32 mL, 2 equiv.) was added in portions while maintaining the reaction temperature below 10° C. After reaction completion (ca. 3 hours), 11 mL of glacial acetic acid followed by 250 mL of methyl tert-butyl ether (MTBE) were added. The layers were separated and the rich organic layer was successively washed with 125 mL of iN aqueous hydrochloric acid and 150 mL of saturated sodium bicarbonate solutions. The rich MTBE solution was solvent exchanged into hexane (i.e., the addition of hexane with concurrent distillation of MTBE) to induce crystallization. The crystal slurry was filtered, washed and dried in vacuo at no more than 25° C., to give 48 g (87 M %, HPLC area % >99) of the title compound.

Workup

  1. temperaturethe slurry was cooled to less than 10° C
  2. temperaturewhile maintaining the reaction temperature below 10° C
  3. additionwere added
  4. customThe layers were separated
  5. washthe rich organic layer was successively washed with 125 mL of iN aqueous hydrochloric acid and 150 mL of saturated sodium bicarbonate solutions
  6. additionthe addition of hexane
  7. distillationwith concurrent distillation of MTBE)
  8. customcrystallization
  9. filtrationThe crystal slurry was filtered
  10. washwashed
  11. customdried in vacuo at no more than 25° C.

Sources & evidence

ORD record
ord-69afbe404c1a4cc59879e5f533798e26
Source dataset
uspto-grants-2001_11
Patent number
US06313308B1

Reaction notes

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