Bromine → HCID 68840689, compound

HRID 1432707Notes

Reaction equation

HRID 1432707 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]2[N:11]([CH2:12][C:13]([F:16])([F:15])[F:14])[N:10]=[CH:9][N:8]=2)[S:5][CH:6]=1.[Br:17]Br>CC(O)=O>[Br:17][C:6]1[S:5][C:4]([C:7]2[N:11]([CH2:12][C:13]([F:14])([F:16])[F:15])[N:10]=[CH:9][N:8]=2)=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 688396375-(4-Chloro-thiophen-2-yl)-1-(2,2,2-trifluoro-ethyl)-1H-[1,2,4]triazole

Product 1

HCID 68840689HCID 68840689, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-(4-chloro-thiophen-2-yl)-1-(2,2,2-trifluoro-ethyl)-1H-[1,2,4]triazole (1.13 g, 4.22 mmol) and AcOH (10 mL) in a sealed tube, is added Br2 (0.23 mL, 4.43 mmol). The solution is heated at 120° C. for 2 hours, and 140° C. for 5 hours. The solution is concentrated, diluted with Et2O (150 mL), washed with sat NaHCO3 (75 mL), sat. Na2S2O3 (75 mL), brine (75 mL) dried over MgSO4, filtered and concentrated. The residue is purified by ISCO flash chromatography (5%-15% EtOAc gradient) furnish the title compound (1.04 g, 3.00 mmol, 71%). 1H NMR (CDCl3) δ 4.88 (q, J=16.0, 7.9 Hz, 2H), 7.22 (s, 1H), 7.99 (s, 1H). LC/MS (m/z): calcd. for C8H4BrClF3N3S (M+H)+: 345.9; found: 346.0.

Workup

  1. concentrationThe solution is concentrated
  2. additiondiluted with Et2O (150 mL)
  3. washwashed with sat NaHCO3 (75 mL), sat. Na2S2O3 (75 mL), brine (75 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by ISCO flash chromatography (5%-15% EtOAc gradient)

Sources & evidence

ORD record
ord-9aece4484ac44a1fab18b5e0006e3622
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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