N-bromobutanimide → HCID 118452550, compound

HRID 1773222Notes

Reaction equation

HRID 1773222 reaction equation
[F:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]2[O:9][C:8]([C:10]#[N:11])=[CH:7][C:6]=2[CH:12]=1.C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:13][C:3]1[C:2]([F:1])=[CH:12][C:6]2[CH:7]=[C:8]([C:10]#[N:11])[O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118452436HCID 118452436, compound

Product 1

HCID 118452550HCID 118452550, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To the solution of 5-fluoro-6-methylbenzofuran-2-carbonitrile (1.44 g, 8.22 mmol) in 82 mL of CCl4 was added NBS (1.536 g, 8.63 mmol) and AlBN (0.067 g, 0.411 mmol). After the reaction mixture was refluxed overnight, the solvent was removed. The residue was purified by silica gel flash chromatography (100% heptane-7% ethyl acetate/heptane) to give 6-(bromomethyl)-5-fluorobenzofuran-2-carbonitrile (1.6 g). 1H NMR (400 MHz, DMSO-d6) δ 4.82 (d, J=1.1 Hz, 2H), 7.75 (d, J=9.5 Hz, 1H), 8.02 (d, J=5.9 Hz, 1H), 8.10 (d, J=0.86 Hz, 1H).

Workup

  1. temperatureAfter the reaction mixture was refluxed overnight
  2. customthe solvent was removed
  3. customThe residue was purified by silica gel flash chromatography (100% heptane-7% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-9110af696b0048729a5e6b3a71011d49
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

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