Acetic Acid → 5-Bromo-2-(4-ethoxyphenyl)thiazole

HRID 56086Notes

Reaction equation

HRID 56086 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:5]=1)[CH3:2].C1C(=O)N([Br:22])C(=O)C1.C(O)(=O)C>C(Cl)Cl>[Br:22][C:12]1[S:11][C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=2)=[N:14][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 691606082-(4-Ethoxyphenyl)thiazole

Product 1

HCID 821347985-Bromo-2-(4-ethoxyphenyl)thiazoleYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-ethoxyphenyl)thiazole (1.03 g, 5.00 mmol) in DCM (30 mL) were added NBS (0.98 g, 5.50 mmol) and acetic acid (0.3 mL) with stirring at rt under N2. The reaction was stirred at 48° C. for 3 h, then cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a white solid (1.34 g, 94%).

Workup

  1. stirringThe reaction was stirred at 48° C. for 3 h
  2. temperaturecooled to rt
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-244122778cf14809b090262dfa40420f
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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