Chlorosulfonic acid → 7-Bromo-dibenzofuran-2-sulfonyl Chloride

HRID 1168244Notes

Reaction equation

HRID 1168244 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][C:11]=2[CH:19]=1.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]3[CH:15]=[C:16]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:17]=[CH:18][C:13]=3[O:12][C:11]=2[CH:19]=1

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 2968613-Bromodibenzofuran

Product 1

HCID 223945507-Bromo-dibenzofuran-2-sulfonyl Chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulfonic acid (3.75 mL, 56 mmoles) was added dropwise to a solution of 3-bromo-dibenzofuran (9.21 g, 37.3 mmoles) in 150 mL of chloroform at room temperature. The reaction was stirred for 5 hours, cooled to 0° C., filtered, and washed the solid with cold dichloromethane. This solid (6.12 g, 18.7 mmoles) was mixed with phosphorous pentachloride (12.9 g, 61.7 mmoles) and the mixture was heated to 110° C. for 4 hours. The mixture was cooled to room temperature and quenched with ice water. Filtered the resulting suspension to give the title compound as a white solid.

Workup

  1. filtrationfiltered
  2. washwashed the solid with cold dichloromethane
  3. temperaturethe mixture was heated to 110° C. for 4 hours
  4. temperatureThe mixture was cooled to room temperature
  5. customquenched with ice water
  6. filtrationFiltered the resulting suspension

Sources & evidence

ORD record
ord-7fa9c74f4d334e0891d2f2c34d1fe2fa
Source dataset
uspto-grants-2003_09
Patent number
US06624177B1

Reaction notes

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