Hydrogen Bromide → 2-Bromo-1-(2-methyl-thiazol-5-yl)-ethanone

HRID 77038Notes

Reaction equation

HRID 77038 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5](C(Cl)=O)[N:6]=1.[N+](=C[Si](C)(C)C)=[N-].[BrH:17].[CH3:18][CH2:19][O:20]C(C)=O>CC#N.O>[Br:17][CH2:18][C:19]([C:4]1[S:3][C:2]([CH3:1])=[N:6][CH:5]=1)=[O:20]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 167693TrimethylsilyldiazomethaneHCID 211839592-Methyl-1,3-thiazole-4-carbonyl chloride

Product 1

HCID 216675822-Bromo-1-(2-methyl-thiazol-5-yl)-ethanoneYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-methylthiazole-4-carbonyl chloride (0.34 g, 2.10 mmol) in dry MeCN (8 mL) cooled at 0° C., under nitrogen atmosphere, is slowly added (diazomethyl)trimethylsilane (3.14 ml, 6.29 mmol, 2.0M in hexane). The reaction is stirred at RT for 15 h (UPLC-MS monitoring: complete conversion). The reaction is cooled at 0° C. and 48% hydrobromic acid (1.23 mL, 7.34 mmol) is added dropwise. The reaction is stirred at RT for 3 hour. Then EtOAc and water are added, the organic layer is separated and the aqueous phase is neutralized with 1M NaOH and extracted with EtOAc. The combined organic layers are dried over Na2SO4, filtered and evaporated to dryness to obtain compound I228 as a dark brown gummy solid (400 mg, 87% yield).

Workup

  1. temperatureThe reaction is cooled at 0° C.
  2. stirringThe reaction is stirred at RT for 3 hour
  3. customthe organic layer is separated
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-13c4ae0ada534e3083770e3250fd1c56
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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