4-Bromophenacyl bromide → 4-(4-Bromo-phenyl)-2-(4-fluoro-phenyl)-thiazole

HRID 651387Notes

Reaction equation

HRID 651387 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)=O>CCO>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:7][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=3)[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 74544-Bromophenacyl bromideHCID 7372234-Fluorothiobenzamide

Product 1

HCID 111749984-(4-Bromo-phenyl)-2-(4-fluoro-phenyl)-thiazoleYield 185.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of p-fluorothiobenzamide (0.39 g, 2.5 mmol) in 20 mL of abs. EtOH is added 2,4′-dibromoacetophenone (0.7 g, 2.5 mmol) all at once. The reaction mixture is stirred at room temperature for 3 hours and then chilled in ice bath. The precipitate is collected by filtration, washed with cold EtOH (5 ml×2) and dried in vacuum to give 2-(4′-fluorophenyl)-4-(4′-bromophenyl)thiazole as a white fluffy crystaline solid (1.55 g, 93%). mp.158-9° C. 1H NMR (CDCl3): δ 7.16 (t, 2H), 7.47 (s, 1H), 7.58 (d, 2H), 7.87 ()d, 2H), 8.02 (m, 2H).

Workup

  1. temperaturechilled in ice bath
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with cold EtOH (5 ml×2)
  4. customdried in vacuum

Sources & evidence

ORD record
ord-ddf4d59357014a4196c1c000f7c3265a
Source dataset
uspto-grants-2001_08
Patent number
US06281217B1

Reaction notes

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