Fluorobenzene → HCID 18986082, compound

HRID 331518Notes

Reaction equation

HRID 331518 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.C(C(/N=N/C(C)(C)C#N)(C)C)#N.[Br:21]N1C(=O)CCC1=O.FC1C=CC=CC=1>>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][Br:21])[CH:3]=1

Participants

5

Reactant 4

HCID 10008FluorobenzeneHCID 67184N-bromobutanimideHCID 27628354-Bromo-2-methylpyridineHCID 178449902HCID 178449902, compound

Product 1

HCID 18986082HCID 18986082, compoundYield 100%

Conditions

Temperature
90 °C

Procedure

4-bromo-2-methyl-pyridine (5 g, 29.07 mmol), 2-[(E)-(1-cyano-1-methyl-ethyl)azo]-2-methyl-propanenitrile (954.7 mg, 5.814 mmol) and N-bromosuccinimide (7.244 g, 40.70 mmol) were added to fluorobenzene (8 mL) and the mixture heated to 90° C. for 1 hour. Reaction mixture was purified by filtering through a silica gel pad and eluting with 50% diethylether/petroleum ether. Product fractions were combined and concentrated in vacuo to give the crude sub-title product (7.294 g, assumed 100% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 4.52 (s, 2H), 7.42 (d, 1H), 7.65 (s, 1H) and 8.42 (d, 1H) ppm.

Workup

  1. customReaction mixture
  2. customwas purified
  3. filtrationby filtering through a silica gel pad
  4. washeluting with 50% diethylether/petroleum ether
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94e2c18d56aa4d7c8735676545ffc834
Source dataset
uspto-grants-2014_11
Patent number
US08877759B2

Reaction notes

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