Chlorosulfonic acid → 5-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfonyl chloride

HRID 584008Notes

Reaction equation

HRID 584008 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][O:7][C:8]1[CH:25]=[CH:24][C:11]([O:12][C:13]2[C:18]([Cl:19])=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:14]=2[Cl:23])=[CH:10][CH:9]=1>>[Cl:19][C:18]1[CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=[C:14]([Cl:23])[C:13]=1[O:12][C:11]1[CH:24]=[CH:25][C:8]([O:7][CH3:6])=[C:9]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:10]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 99729021,3-Dichloro-2-(4-methoxyphenoxy)-5-nitrobenzene

Product 1

HCID 155414425-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfonyl chloride

Conditions

Temperature
0 °C

Procedure

To cooled chlorosulfonic acid (2.0 mL) at 0° C. was added 4-(4-methoxy-phenoxy)-3,5-dichloro-nitrobenzene (700 mg, 2.2 mmol) in several portions. The resulting mixture was stirred at 0° C. for 5 min, then at RT for 2.5 h. The solution was added dropwise to ice water (40 mL) and the product was extracted with EtOAc (3×50 mL). The combined organic extracts were dried and concentrated to yield the title compound of Step A (920 mg) as a crude product which was used in the next step without purification. MS (APCl−) Calc.: 410.9. Found: 392.1 (M−1−Cl+OH, sulfonic acid).

Workup

  1. waitat RT for 2.5 h
  2. extractionthe product was extracted with EtOAc (3×50 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4132ef1a84be4322bf15315ccfbdbd31
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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