4-Iodophenol → 2-(4-Iodo-phenoxymethyl)-thiazole-4-carboxylic acid ethyl ester

HRID 2112994Notes

Reaction equation

HRID 2112994 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]([C:12]1[N:13]=[C:14]([CH2:17]Br)[S:15][CH:16]=1)=[O:11])[CH3:8].[I:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>CC(C)=O>[CH2:7]([O:9][C:10]([C:12]1[N:13]=[C:14]([CH2:17][O:26][C:23]2[CH:24]=[CH:25][C:20]([I:19])=[CH:21][CH:22]=2)[S:15][CH:16]=1)=[O:11])[CH3:8]

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 11043146Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 576433502-(4-Iodo-phenoxymethyl)-thiazole-4-carboxylic acid ethyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ground potassium carbonate (3.4 g, 24.6 mmol) was added to a solution of 2-bromomethyl-thiazole-4-carboxylic acid ethyl ester (12.83 g, 56 mmol; from Step 1 above) and 4-iodophenol (5.5 g, 25 mmol; available from Aldrich Chemical Company, Inc., Milwaukee, Wis.) in acetone (440 mL). The reaction mixture was heated at reflux for 15 h and then it was filtered and water was added to the filtrate until it turned cloudy. The filtrate was left on ice and then the resulting white solid was filtered off, washed with acetone/hexanes (2:1) and dried to give 2-(4-iodo-phenoxymethyl) -thiazole-4-carboxylic acid ethyl ester (5.6 g, 65%) as a white solid. 1HNMR (CDCl3): δ 1.4 (t, 3H, J=7 Hz), 4.46 (q, 2H, J=7 Hz), 5.4 (s, 2H), 6.7 (d, 2H, J=9 Hz), 7.6 (d, 2H, J=9 Hz), 8.2 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 15 h
  3. filtrationit was filtered
  4. additionwater was added to the filtrate until it
  5. waitThe filtrate was left on ice
  6. filtrationthe resulting white solid was filtered off
  7. washwashed with acetone/hexanes (2:1)
  8. customdried

Sources & evidence

ORD record
ord-3d7f91870658478b9bc816d97290f742
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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