Water → 2-Bromo-4-fluoro-6-nitroaniline

HRID 475143Notes

Reaction equation

HRID 475143 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12]Br.O>C(Cl)Cl.CC(O)=O>[Br:12][C:7]1[CH:8]=[C:2]([F:1])[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]=1[NH2:6]

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 677694-Fluoro-2-nitroaniline

Product 1

HCID 2920042-Bromo-4-fluoro-6-nitroanilineYield 140%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-fluoro-2-nitroaniline (10.0 g, 42.55 mmol) in DCM (150 mL) and HOAc (75 mL) at 0° C. was added dropwise Br2 (9.9 ml, 130 mmol) at a rate to maintain the internal reaction temperature below 10° C. The reaction mixture was stirred at RT overnight and then poured into water (500 mL), followed by separation of the organic phase. The pH of the aqueous phase was adjusted to about 7 by adding NH4OH, and the mixture was extracted with DCM (100 mL×3). The combined extracts were dried (MgSO4), filtered, and concentrated in vacuo to afford 2-bromo-4-fluoro-6-nitroaniline as a yellow solid (14 g, 93%). MS (ESI): m/z=233 [M−1]−.

Workup

  1. temperatureto maintain the internal reaction temperature below 10° C
  2. customfollowed by separation of the organic phase
  3. additionby adding NH4OH
  4. extractionthe mixture was extracted with DCM (100 mL×3)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18ace49ab9f14da486010cea5de0f2be
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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