Bromine → 2-Bromo-1-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazol-4-yl]-ethanone

HRID 1258877Notes

Reaction equation

HRID 1258877 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[C:14](=[O:16])[CH3:15])=[CH:4][CH:3]=1.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[Br:41]Br>C(Cl)(Cl)Cl>[Br:41][CH2:15][C:14]([C:9]1[N:10]([CH3:13])[N:11]=[N:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:16]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 679548121-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazol-4-yl]-ethanone

Product 1

HCID 885313192-Bromo-1-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazol-4-yl]-ethanoneYield 63.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-ethanone (4.02 g, 18.34 mmol) was dissolved in chloroform (18 mL) and acetic (0.36 mL) was heated to reflux and then a solution of bromine (1.04 mL, 20.17 mmol) in chloroform (9 mL) was added dropwise within 10 min at and after 1 h bromine (0.10 mL, 2.02 mmol) was added and heated under reflux for 1 h. After cooling to room temperature the mixture was poured onto ice-water and the mixture extracted with dichloromethane. The combined organic extracts were washed with water, brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (3.48 g, 63%) as a light red solid. MS: m/e=298.1/300.1 [M+H]+.

Workup

  1. temperatureto reflux
  2. additionwas added
  3. temperatureheated
  4. temperatureunder reflux for 1 h
  5. additionwas poured onto ice-water
  6. extractionthe mixture extracted with dichloromethane
  7. washThe combined organic extracts were washed with water, brine
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-85cf64cd6d594af2b2f704d94cd92c96
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

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