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

HRID 1180261Notes

Reaction equation

HRID 1180261 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 sulphuric acid (3.15 g, 32.2 mmol). The slurry was warmed to 70° C. and the resulting solution stirred for 7 h then stood 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 filtered, 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 I, CDCl3) 6.97-7.08 (1H, m), 7.38-7.54 (2H, m), 7.62-7.68 (1H, m).

Workup

  1. waitthen stood at ambient temperature for 18 h
  2. customthe product rapidly crystallised
  3. waitThe slurry was left
  4. stirringto stir for 0.5 h
  5. filtrationthen filtered
  6. washwashed with 1:1 acetonitrile/water (10 ml)
  7. waitleft
  8. customto air-dry

Sources & evidence

ORD record
ord-315227baea1447bdae4a88a7116c241b
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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