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

HRID 1258908Notes

Reaction equation

HRID 1258908 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13](=[O:15])[CH3:14])=[C:11]([CH3:16])[N:10]=[N:9]2)=[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][CH2:14][C:13]([C:12]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]=[N:10][C:11]=1[CH3:16])=[O:15]

Participants

5

Reactant 3

HCID 24408BromineHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 679549821-[3-(4-Fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-ethanone

Product 1

HCID 885313122-Bromo-1-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-ethanoneYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-ethanone (3.62 g, 17 mmol) was dissolved in chloroform (28 mL) and acetic (0.5 mL) was heated to reflux and then a solution of bromine (0.89 mL, 17 mmol) in chloroform (9 mL) and heated under reflux for 2 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, 10 to 60% ethyl acetate in heptane) afforded the title compound (3.34 g, 68%) as an off white solid. MS: m/e=298.3/300.2 [M+H]+.

Workup

  1. temperatureto reflux
  2. temperatureunder reflux for 2 h
  3. additionwas poured onto ice-water
  4. extractionthe mixture extracted with dichloromethane
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by chromatography (silica, 10 to 60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-115fcb597ca64cb89f8c1c6738b9b1f2
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

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