Bromine → 4-Bromo-2-fluoro-6-methoxyaniline hydrobromide

HRID 1487677Notes

Reaction equation

HRID 1487677 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:3]=1[NH2:4].[Br:11]Br>C(O)(=O)C>[BrH:11].[Br:11][C:7]1[CH:6]=[C:5]([O:9][CH3:10])[C:3]([NH2:4])=[C:2]([F:1])[CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 4592532-Fluoro-6-methoxyaniline

Product 1

HCID 867265044-Bromo-2-fluoro-6-methoxyaniline hydrobromideYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 2-fluoro-6-methoxyaniline (1 equiv) in acetic acid (0.7 M) was cooled to 5° C. A mixture of bromine (0.9 equiv) in acetic acid (0.7 M) was slowly added. The reaction mixture was stirred for 2 h at 5° C. The resulting solid was filtered, washed with ether, and dried to give the title compound (90% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 3.84 (s, 3H) 6.79 (br. s., 2H) 6.97 (s, 1H) 7.06 (d, J=10.09 Hz, 1H). MS (ESI) m/z 219.9 [M+H]+.

Workup

  1. additionwas slowly added
  2. filtrationThe resulting solid was filtered
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-1455cc0206ef4340b569ca13cd9dd701
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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