Acetic Acid → 2-Bromo-4-fluoro-(methyloxy)aniline

HRID 639011Notes

Reaction equation

HRID 639011 reaction equation
CO[C:3]1[CH:8]=[C:7]([N+:9]([O-])=[O:10])[C:6]([Br:12])=[CH:5][C:4]=1[F:13].[C:14](O)(=O)C.C(O)C.C(=O)([O-])[O-].[K+].[K+]>O.[Fe]>[Br:12][C:6]1[CH:5]=[C:4]([F:13])[CH:3]=[CH:8][C:7]=1[NH:9][O:10][CH3:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 11430Potassium CarbonateHCID 179763101-Bromo-5-fluoro-4-methoxy-2-nitrobenzene

Product 1

HCID 866167832-Bromo-4-fluoro-(methyloxy)anilineYield 67%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-bromo-2-fluoro-5-nitrophenyl methyl ether (25.5 g, 102 mmol), acetic acid (250 mL), ethanol (250 mL) and iron powder (22.7 g, 408 mmol) was heated to 100 C for 4 hours. The reaction mixture was cooled to room temperature, diluted with water, neutralised by addition of potassium carbonate and filtered through Celite. The aqueous layer was extracted thrice with DCM. The combined organic layers were dried over magnesium sulfate and evaporated under vacuum to afford the title compound (15 g, 67%) as a white solid. LC-MS (ES) (M+H)+ m/z=220.

Workup

  1. temperaturewas heated to 100 C for 4 hours
  2. filtrationfiltered through Celite
  3. extractionThe aqueous layer was extracted thrice with DCM
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-4580695b6e6a478b8f5e304c89b48a1d
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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