Chlorosulfonic acid → 7-Nitrodibenzo[b,d]furan-2-sulfonyl chloride

HRID 1008505Notes

Reaction equation

HRID 1008505 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[CH:16]=1)([O-:3])=[O:2].[Cl:17][S:18](O)(=[O:20])=[O:19]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:11]3[CH:12]=[C:13]([S:18]([Cl:17])(=[O:20])=[O:19])[CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[CH:16]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 728973-Nitrodibenzofuran

Product 1

HCID 109030227-Nitrodibenzo[b,d]furan-2-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 100 mg of 3-nitrodibenzofuran in 1.7 mL of dichloromethane at −20° C. under a nitrogen atmosphere was added 0.44 mL chlorosulfonic acid in small portions. The reaction mixture was allowed to slowly warm to room temperature and stirred for 66 hours at room temperature. The reaction mixture was poured into ice-cold water, extracted four times with dichloromethane, dried (magnesium sulfate) and concentrated. Purification on silica gel (dichloromethane) yielded 129 mg of 50a: rf=0.73.

Workup

  1. additionThe reaction mixture was poured into ice-cold water
  2. extractionextracted four times with dichloromethane
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customPurification on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-12511a493ab94a8fa2f6327ca90a0e6c
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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