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

HRID 1880971Notes

Reaction equation

HRID 1880971 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, 3 H) 6.42 (dd, J=8.6, 1.8 Hz, 1 H) 7.01 (dd, J=8.6, 7.1 Hz, 1 H). [M+H] calc'd for C7H7BrFNO, 222; found 222.

Workup

  1. filtrationSolid was filtered
  2. washwashed with acetic acid

Sources & evidence

ORD record
ord-d2449c284d644b7fb87e6f1b3250cd4a
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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