Water → HCID 22065166, compound

HRID 497541Notes

Reaction equation

HRID 497541 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)[S:16][CH:15]=2)[N:11]([CH3:30])[N:10]=1.[Br:31]Br.O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[CH:21][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:23][CH:24]=3)[S:16][C:15]=2[Br:31])[N:11]([CH3:30])[N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 22065110HCID 22065110, compound

Product 1

HCID 22065166HCID 22065166, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(2-chloro-6-fluorophenyl)-1-methyl-5-[5-(4-trifluoromethoxyphenyl)thien-3-yl]-1H-1,2,4-triazole (0.26 g, 0.6 mmol) in glacial acetic acid (7 mL) was cooled to 6° C. Bromine (0.1 g, 32 μL, 0.6 mmol) was added to the reaction and allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was poured into water (50 mL) and extracted with ether (3×30 mL). The combined ethereal extracts were washed with water (100 mL), saturated aqueous sodium bicarbonate (100 mL), aqueous sodium bisulphite (10% solution, 50 mL) and brine (70 mL), dried over magnesium sulphate and concentrated. Column chromatography gave the product (297 mg, 97%) as a yellowish solid: mp 135-136° C.; 1H NMR (CDCl3) δ 7.57 (d, 1H), 7.25-7.40 (m, 5H), 7.12 (t, 1H), 4.04 (s, 3H); EI/MS 533 m/e (M+).

Workup

  1. extractionextracted with ether (3×30 mL)
  2. washThe combined ethereal extracts were washed with water (100 mL), saturated aqueous sodium bicarbonate (100 mL), aqueous sodium bisulphite (10% solution, 50 mL) and brine (70 mL)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e356c3cb45d342819fa2380beb4bd503
Source dataset
uspto-grants-2005_09
Patent number
US06949576B2

Reaction notes

Loading…