1,2-Dimethoxyethane → 4-(Thiophen-3-yl)aniline

HRID 2375441Notes

Reaction equation

HRID 2375441 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].COCCOC.Br[C:14]1[CH:18]=[CH:17][S:16][CH:15]=1.CC1(C)C(C)(C)OB([C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)O1>O.C(OCC)(=O)C>[S:16]1[CH:17]=[CH:18][C:14]([C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)=[CH:15]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 133833-BromothiopheneHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 41303364-(Thiophen-3-yl)aniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

An aqueous sodium carbonate solution and tetrakis triphenylphosphine palladium were added to a DME solution of 3-bromothiophene and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, and the mixture was refluxed under heating for 6 hours with argon atmosphere. After cooling to room temperature, the reaction mixture was added with ethyl acetate and water to separate an organic layer, which was then washed and dried. The solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography, to obtain 4-(3-thienyl)aniline (pale yellow solid). Electron Impact-MS (M)+: 175.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 6 hours with argon atmosphere
  3. customto separate an organic layer, which
  4. washwas then washed
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customThe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eb20971a55594cf79ce5e472d73e8d0b
Source dataset
uspto-grants-2008_12
Patent number
US07465748B2

Reaction notes

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