Hydrogen Bromide → 6-Chloro-3,3-dimethyl-benzo[1,4]oxathiin-2-one

HRID 11691Notes

Reaction equation

HRID 11691 reaction equation
CO[C:3](=[O:17])[C:4]([S:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[O:15]C)([CH3:6])[CH3:5].Br>>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]2[O:15][C:3](=[O:17])[C:4]([CH3:5])([CH3:6])[S:7][C:8]=2[CH:13]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 69655887HCID 69655887, compound

Product 1

HCID 219733516-Chloro-3,3-dimethyl-benzo[1,4]oxathiin-2-one

Procedure

To 2-(5-chloro-2-methoxy-phenylsulfanyl)-2-methyl-propionic acid methyl ester (prepared from 5-chloro-2-methoxy-benzenesulfonyl chloride: Syn. Comm., (2001), 31, 505–510) (0.25 g, 0.9 mmol) was added 48% hydrobromic acid (5 ml). The reaction was heated to reflux for 24 hours at which time the solvent was removed by evaporation. To the crude acid phenol was added toluene (5 ml) and catalytic pyridinium p-toluenesulfonate. After 12 hours of heating at reflux the reaction was concentrated and the title compound was isolated by chromatography on silica gel (0.27 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 24 hours at which time the solvent
  3. customwas removed by evaporation
  4. additionTo the crude acid phenol was added toluene (5 ml) and catalytic pyridinium p-toluenesulfonate
  5. temperatureAfter 12 hours of heating
  6. temperatureat reflux the reaction
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-7dff17e2356f4c31aafbe369d51ba4d7
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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