N-bromobutanimide → HCID 86721321, compound

HRID 2175388Notes

Reaction equation

HRID 2175388 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[C:5]#[N:6].C1C(=O)N([Br:18])C(=O)C1>C(#N)C>[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([Br:18])=[C:4]([CH:3]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 152516943-Amino-4-fluorobenzonitrile

Product 1

HCID 86721321HCID 86721321, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-amino-4-fluorobenzonitrile (9.82 g, 72.1 mmol) was dissolved in acetonitrile to give a pale yellow solution. NBS (13.5 g, 75.7 mmol) was added in portions; the reaction mixture turned brown-blackish but remained a solution. After the completion of the reaction was confirmed by TLC and HPLC, silica gel was added to the reaction mixture and the solvent was evaporated under reduced pressure. The crude product was leaded on a CombiFlash column (330 g) and the product was eluted with hexanes/ethyl acetate (0→15% gradient). The clean fractions were combined to give 9.63 g (62%) of a yellowish off-white solid. More product was found in mixed fractions which were discarded. 1H NMR (300 MHz, dmso) δ 7.57 (d, J=10.9 Hz, 1H), 7.17 (d, J=8.7 Hz, 1H), 5.85 (s br, 2H); MS (ES) 213/215 (M−H).

Workup

  1. customto give a pale yellow solution
  2. additionwas added to the reaction mixture
  3. customthe solvent was evaporated under reduced pressure
  4. washthe product was eluted with hexanes/ethyl acetate (0→15% gradient)

Sources & evidence

ORD record
ord-9a11aa2a08704e3a9d9bbfe147196a27
Source dataset
uspto-grants-2015_06
Patent number
US09062068B2

Reaction notes

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