4-Bromoanisole → HCID 86675423, compound

HRID 1474422Notes

Reaction equation

HRID 1474422 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][C:4]=1[NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16].[Cl-].[Al+3].[Cl-].[Cl-].[Br:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1>ClCCCl>[Br:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[C:29]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH:5]=2)(=[O:11])=[O:10])[CH:30]=1

Participants

5

Reactant 3

HCID 77304-BromoanisoleHCID 6451240Aluminum(III) ChlorideHCID 54897518HCID 54897518, compound

Product 1

HCID 86675423HCID 86675423, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a 500 mL 3-neck round bottom flask equipped with reflux condenser, N2 inlet, thermometer socket and magnetic bar inside was added 4-Methoxy-3-(2,2,2-trifluoroacetylamino)benzenesulfonyl chloride (17 grams, 53.5 mmol) in 1,2-dichloroethane (200 mL). To the stirred solution of above reactions mass, Aluminium chloride (7.86 grams, 58.89 mmol) and 4-bromo anisole (20 grams, 107 mmol) were added slowly. Then the reaction mass was stirred under reflux temperature for 20 hours. Reaction mass was quenched into ice cold water and acidified with 2N hydrochloric acid (50 mL) until the pH was ˜4 and extracted the product with ethyl acetate (3×200 mL). The combined organic layers were washed with brine solution (1×50 mL), dried over anhydrous sodium sulfate and solvent was removed under reduced pressure to obtain the technical product. It was further purified by column chromatography to obtain the title product, the eluent being 15% ethyl acetate in n-hexane. Yield: 18.4 grams

Workup

  1. customIn a 500 mL 3-neck round bottom flask equipped
  2. temperaturewith reflux condenser, N2 inlet
  3. temperatureunder reflux temperature for 20 hours
  4. customReaction mass
  5. customwas quenched into ice cold water
  6. extractionextracted the product with ethyl acetate (3×200 mL)
  7. washThe combined organic layers were washed with brine solution (1×50 mL)
  8. dry with materialdried over anhydrous sodium sulfate and solvent
  9. customwas removed under reduced pressure
  10. customto obtain the technical product
  11. customIt was further purified by column chromatography

Sources & evidence

ORD record
ord-90bedd9ff60f4d278102610875f88273
Source dataset
uspto-grants-2015_04
Patent number
US09018231B2

Reaction notes

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