Bromine → 4-Bromo-3-fluoro-2-methoxyaniline

HRID 914200Notes

Reaction equation

HRID 914200 reaction equation
[F:1][C:2]1[C:3]([O:9][CH3:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Br:11]Br>C(O)(=O)C>[Br:11][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([O:9][CH3:10])[C:2]=1[F:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 5811093-Fluoro-2-methoxyaniline

Product 1

HCID 579555294-Bromo-3-fluoro-2-methoxyaniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To 3-fluoro-2-methoxyaniline (2.8 g, 20 mmol) in 10 mL of acetic acid was added bromine (0.82 mL, 16 mmol) in acetic acid (10 mL) dropwise. The reaction mixture was stirred at rt. for 30 min. Solid was filtered and washed with acetic acid to give the HBr salt. It was then dissolved in water, basified by addition of KOH, extracted with ethyl acetate. The organic layer was dried and concentrated to give a white solid (2.8 g, 80%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.93 (s, 3H) 6.42 (dd, J=8.6, 1.8 Hz, 1H) 7.01 (dd, J=8.6, 7.1 Hz, 1H). [M+H] calc'd for C7H7BrFNO, 222. found 222.

Workup

  1. filtrationSolid was filtered
  2. washwashed with acetic acid

Sources & evidence

ORD record
ord-da33d014c073458f8ca5001840db23d0
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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