p-Toluenesulfonic acid monohydrate → HCID 57863119, compound

HRID 418128Notes

Reaction equation

HRID 418128 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:5]=[C:4]([O:14]COC)[CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]([OH:14])[CH:5]=[C:6]([S:8]([CH:11]([CH3:12])[CH3:13])(=[O:9])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57863096HCID 57863096, compound

Product 1

HCID 57863119HCID 57863119, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-bromo-3-methoxymethoxy-5-(propane-2-sulfonyl)-benzene (840 mg, 2.59 mmol) in THF (24.4 mL) and methanol (40 mL) was added p-toluenesulfonic acid hydrate (150 mg, 0.78 mmol) at room temperature. Then, the resulting solution was heated to 70° C. and stirred for 2 days. Then, the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude residue which was purified by using an ISCO 40 g column chromatography, eluting with 5-30% ethyl acetate in hexanes to isolate 3-bromo-5-(propane-2-sulfonyl)-phenol (354 mg, 49%) as a viscous oil: ES(+)-HRMS m/e calcd for C9H11BrO3S (M+Na)+ 300.9504, found 300.9505.

Workup

  1. temperatureThen, the reaction mixture was cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. customThe crude residue which was purified
  4. washeluting with 5-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6335e72e9bb642df818627aa0664d9fd
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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