4-Bromoaniline → HCID 3651415, compound

HRID 1410239Notes

Reaction equation

HRID 1410239 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].O=S(Cl)Cl.[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>CN(C=O)C.C(Cl)Cl>[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 78074-BromoanilineHCID 24386Thionyl ChlorideHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 3651415HCID 3651415, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-fluoro-3-nitrobenzoic acid (10.0 g; 54.0 mmol), SOCl2 (20.0 mL; 270 mmol) and DMF (2-3 drops) was refluxed for 4 h, concentrated and the residue was dissolved in DCM (25 mL) and slowly added to a mixture of 4-bromoaniline (9.3 g; 54.1 mmol) and TEA (11.4 mL; 81.0 mmol) in DCM (50 mL) at 0° C. The mixture was stirred for 1 h at rt, concentrated, EtOAc was added and the organic phase was washed with aqueous NaHCO3, aqueous HCl (1 M), dried over Na2SO4, filtered and concentrated to give the sub-title compound. Yield: 18.0 g (98%).

Workup

  1. temperaturewas refluxed for 4 h
  2. concentrationconcentrated
  3. dissolutionthe residue was dissolved in DCM (25 mL)
  4. concentrationconcentrated
  5. additionEtOAc was added
  6. washthe organic phase was washed with aqueous NaHCO3, aqueous HCl (1 M)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-af765a9b4d084a75a23b627646e1b1b2
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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