2-Trimethylsilylthiazole → 2-(4-Bromo-2-methyl-benzoyl)-thiazole

HRID 1017781Notes

Reaction equation

HRID 1017781 reaction equation
C[Si](C)(C)[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[C:13]([CH3:20])[CH:12]=1>C(OCC)(=O)C>[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([C:3]2[S:4][CH:5]=[CH:6][N:7]=2)=[O:16])=[C:13]([CH3:20])[CH:12]=1

Participants

4

Reactant 2

HCID 5884532-TrimethylsilylthiazoleHCID 128464834-Bromo-2-methylbenzoyl chloride

Product 1

HCID 184050062-(4-Bromo-2-methyl-benzoyl)-thiazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2.0 g (13 mmol) of 2-trimethylsilylthiazole and 6.1 g (26 mmol) of 4-bromo-2-methyl-benzoic acid chloride are combined while cooling with an ice bath and then are heated to 80° C. for 3 hours. The crude product is taken up in 30 ml of ethyl acetate, washed with H2O, saturated NaHCO3 solution and H2O, dried and purified by flash chromatography (silica gel; methylene chloride).

Workup

  1. temperaturewhile cooling with an ice bath
  2. washwashed with H2O, saturated NaHCO3 solution and H2O
  3. customdried
  4. custompurified by flash chromatography (silica gel; methylene chloride)

Sources & evidence

ORD record
ord-f99fb36b246243e48267fec2d2644bc8
Source dataset
uspto-grants-2002_11
Patent number
US06479524B1

Reaction notes

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