Hydrochloric Acid → 5-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfinic acid

HRID 432927Notes

Reaction equation

HRID 432927 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17]([Cl:24])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([S:11](Cl)(=[O:13])=[O:12])[CH:10]=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].Cl>O>[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17]([Cl:24])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([S:11]([OH:13])=[O:12])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 155414425-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfonyl chloride

Product 1

HCID 223448795-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfinic acidYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfonyl chloride (4.26 g, 10.3 mmol) in water (40 mL) was added sodium sulfite (3.89 g, 30.9 mmol) and sodium bicarbonate (5.19 g, 61.8 mmol). The resulting mixture was heated to reflux for 2 h and then cooled to RT. The solution was acidified with conc. HCl (5 mL) followed by addition of water (40 mL). The aqueous solution was extracted with EtOAc (5×80 mL). The combined organic extracts were washed with brine (2×50 mL), dried and concentrated to give the title compound of Step B (2.56 g) as a solid. The title product of Step B was used in the next step without purification. MS (APCl−) Calc.: 376.9, Found: 375.8 (M−1).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h
  3. extractionThe aqueous solution was extracted with EtOAc (5×80 mL)
  4. washThe combined organic extracts were washed with brine (2×50 mL)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55f17418a8184f56b72631e68bac29be
Source dataset
uspto-grants-2003_12
Patent number
US06664291B2

Reaction notes

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