Bromine → 2-Bromo-1-(1-(2-fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)ethanone

HRID 1258913Notes

Reaction equation

HRID 1258913 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13](=[O:15])[CH3:14])=[C:11]([CH3:16])[N:10]=[N:9]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:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:9]=[N:10][C:11]=1[CH3:16])=[O:15]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 679550691-(1-(2-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)ethanone

Product 1

HCID 885312192-Bromo-1-(1-(2-fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)ethanoneYield 68.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1-(1-(2-fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)ethanone (1.66 g, 7.57 mmol) was dissolved in chloroform (12 mL) and acetic (0.24 mL) was heated to reflux and then a solution of bromine (0.41 mL, 7.95 mmol) in chloroform (5 mL) and heated under reflux for 2 h and then bromine (0.12 mL, 2.27 mmol) in chloroforom (2 mL) was added and heated under reflux for a further 30 min. 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 (1.54 g, 64%) as an off white solid. MS: m/e=298.1/300.0 [M+H]+.

Workup

  1. temperatureto reflux
  2. temperatureunder reflux for 2 h
  3. temperatureheated
  4. temperatureunder reflux for a further 30 min
  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, 10 to 60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-7648c969df8a4285a06db56b515f2b68
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

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