Water → 3'-Bromo-4,2',6'-trifluorobiphenyl-2-carbonitrile

HRID 891870Notes

Reaction equation

HRID 891870 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:16]#[N:17])[C:5]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[F:15])=[CH:6][CH:7]=1.[Br:18]N1C(C)(C)C(=O)N(Br)C1=O.S(=O)(=O)(O)O.O>C(#N)C>[Br:18][C:12]1[C:13]([F:14])=[C:8]([C:5]2[C:4]([C:16]#[N:17])=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([F:15])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 222401054,2',6'-Trifluorobiphenyl-2-carbonitrile

Product 1

HCID 222401013'-Bromo-4,2',6'-trifluorobiphenyl-2-carbonitrileYield 171.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a slurry of 4,2′,6′-trifluorobiphenyl-2-carbonitrile (5.0 g, 21.4 mmol) and 1,3-dibromo-5,5-dimethylhydantoin (3.37 g, 11.8 mmol) in acetonitrile (45 ml) was added concentrated sulfuric acid (3.15 g, 32.2 mmol). The slurry was warmed to 70° C. and the resulting solution stirred for 7 h then aged at ambient temperature for 18 h. Water (45 ml) was added dropwise to the solution over 15 min. The layers were allowed to settle and the product rapidly crystallised. The slurry was left to stir for 0.5 h then the solid was collected by filtration, washed with 1:1 acetonitrile:water (10 ml) and left to air dry, which gave 3′-bromo-4,2′,6′-trifluorobiphenyl-2-carbonitrile (6.3 g, 94%) as a white solid: δH (360 MHz, CDCl3) 6.97–7.08 (1H, m), 7.38–7.54 (2H, m), 7.62–7.68 (1H, m).

Workup

  1. waitthen aged at ambient temperature for 18 h
  2. customthe product rapidly crystallised
  3. waitThe slurry was left
  4. stirringto stir for 0.5 h
  5. filtrationthe solid was collected by filtration
  6. washwashed with 1:1 acetonitrile
  7. waitwater (10 ml) and left to air
  8. customdry

Sources & evidence

ORD record
ord-36c80e8890d04a348a60a3619b07600f
Source dataset
uspto-grants-2006_02
Patent number
US07005431B2

Reaction notes

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