N-bromobutanimide → 5-Amino-2-bromo-6-fluoro-4-methoxybiphenyl-3-carbonitrile

HRID 17524Notes

Reaction equation

HRID 17524 reaction equation
[NH2:1][C:2]1[C:3]([O:17][CH3:18])=[C:4]([C:15]#[N:16])[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]=1[F:8].[Br:19]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:1][C:2]1[C:3]([O:17][CH3:18])=[C:4]([C:15]#[N:16])[C:5]([Br:19])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 860975065-Amino-6-fluoro-4-methoxybiphenyl-3-carbonitrile

Product 1

HCID 860975085-Amino-2-bromo-6-fluoro-4-methoxybiphenyl-3-carbonitrileYield 89.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Amino-6-fluoro-4-methoxybiphenyl-3-carbonitrile (I-234) (500 mg, 2.06 mmol) was dissolved in acetic acid (9.5 ml), and at room temperature, N-bromosuccinimide (441 mg, 2.48 mmol) was gradually added. After stirring under nitrogen atmosphere at room temperature for 1 hour, the solvent was evaporated away under reduced pressure. The residue was fractionated with ethyl acetate and aqueous 1M sodium hydroxide solution. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=3:1) to obtain the entitled compound (592 mg, 89%) as a pale brown solid.

Workup

  1. customthe solvent was evaporated away under reduced pressure
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated away
  6. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-618182d5fd9d4d75b4fee67d0e8f90e2
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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