Dimethylformamide → 4-Phenoxybenzene-1-sulfonyl chloride

HRID 651338Notes

Reaction equation

HRID 651338 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C>ClCCl>[O:12]([C:13]1[CH:14]=[CH:15][C:16]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7583Diphenyl EtherHCID 24638Chlorosulfonic acidHCID 65578Oxalyl chloride

Product 1

HCID 27947564-Phenoxybenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of chlorosulfonic acid (4.3 mL, 64.6 mmol) in dichloromethane (20 mL) is added dropwise to a solution of diphenyl ether (10 g, 58.8 mmol) in dichloromethane (20 mL) at 0° C. under nitrogen atmosphere. The reaction mixture is slowly warmed up to RT and stirred for 2 h. To the mixture are added oxalyl chloride (6.5 ml, 76.4 mmol) and then DMF (1.5 mL) at RT. After being heated at 40° C. for 1 h, the reaction mixture is stirred at RT for 15 h. The mixture is poured to ice-water and extracted with ether. The organic layer is dried over MgSO4 and evaporated in vacuo to give the title compound quantitatively: NMR (CDCl3) 7.10 (t, 4H, J=8.6 Hz), 7.22-7.30 (m, 1 H), 7.46 (t, 2H, J=8.6 Hz), 7.98 (d, 2H, J=9.1 Hz).

Workup

  1. customat RT
  2. temperatureAfter being heated at 40° C. for 1 h
  3. stirringthe reaction mixture is stirred at RT for 15 h
  4. extractionextracted with ether
  5. dry with materialThe organic layer is dried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b7ac400462ee40d0b8ba3dd2953d523e
Source dataset
uspto-grants-2001_08
Patent number
US06277987B1

Reaction notes

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