Hydrochloric Acid → HCID 89932943, compound

HRID 1775438Notes

Reaction equation

HRID 1775438 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][CH2:12]O)[C:3]=1[OH:14].CS(Cl)(=O)=O.C(=O)([O-])O.[Na+].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]2[O:14][CH2:12][CH2:11][C:4]=2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 118071526HCID 118071526, compound

Product 1

HCID 89932943HCID 89932943, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-15 °C

Procedure

A mixture of 2-chloro-6-(2-hydroxyethyl)-4-nitrophenol (11.3 g) and pyridine (41.8 mL) was cooled to −15° C. To this mixture was added dropwise methanesulfonyl chloride (4.04 mL), followed by stirring at −10° C. for 30 minutes. To this reaction mixture was added methanesulfonyl chloride (2.02 mL), followed by stirring at −10° C. for 20 minutes. To the mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by stirring for 2 hours, the pH was adjusted to 1 with 6 M hydrochloric acid, followed by extraction with ethyl acetate, and the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration, the filtrate was concentrated under reduced pressure, and then the obtained residue was dissolved in ethyl acetate. To this mixture was added triethylamine (18.1 mL), followed by stirring at 78° C. overnight. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 70:30) to obtain 7-chloro-5-nitro-2,3-dihydro-1-benzofuran (7.75 g) as a yellow solid.

Workup

  1. stirringby stirring at −10° C. for 20 minutes
  2. stirringby stirring for 2 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble materials were separated by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionthe obtained residue was dissolved in ethyl acetate
  9. additionTo this mixture was added triethylamine (18.1 mL)
  10. stirringby stirring at 78° C. overnight
  11. temperatureAfter cooling to room temperature
  12. concentrationthe reaction mixture was concentrated under reduced pressure
  13. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-26a8bb6a532a4c0b8f76e38498d0b66e
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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