Bromine → HCID 88531522, compound

HRID 1258891Notes

Reaction equation

HRID 1258891 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:16])[C:12]=1[C:13](=[O:15])[CH3:14].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:11]([CH3:16])[N:10]=[N:9][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])=[O:15]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 67955518HCID 67955518, compound

Product 1

HCID 88531522HCID 88531522, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A solution of 1-(4-(2-chlorophenyl)-1-methyl-1H-1,2,3-triazol-5-yl)ethanone (1.02 g, 4.33 mmol) was dissolved in chloroform (7 mL) and acetic (0.136 mL) was heated to reflux and then a solution of bromine (0.234 mL, 4.54 mmol) in chloroform (3 mL) was added dropwise within 10 min at and after 1 h bromine (0.09 mL, 1.73 mmol) in chloroform (2 mL) 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, 10 to 60% ethyl acetate in heptane) afforded the title compound (988 mg, 73%) as an off white solid. MS: m/e=313.9/315.9 [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, 10 to 60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-f1f58c5621a046b4af6384a4faa98f73
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

Loading…