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

HRID 636932Notes

Reaction equation

HRID 636932 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-d668e9cb891f43bd86cb6b09ecb2adbd
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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