4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

Base Information

• Chemical Name: 4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole
• CAS No.: 292073-43-9
• Molecular Formula: C₂₄H₃₀BrNOSSi
• Molecular Weight: 488.564
• Mol file: 292073-43-9.mol

Synonyms:4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

Chemical Property of 4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

There total 16 articles about 4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole (292073-56-4) → 4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole (292073-43-9)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(03)01020-2

Reference yield:

methanesulfonic acid 2-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-thiazol-4-ylmethyl ester → 4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole (292073-43-9)

Guidance literature:

With lithium bromide; In dichloromethane; acetone; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(03)01020-2

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole (292073-43-9)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 14 h / 20 °C

2: DIBAL / diethyl ether; hexane / 0.5 h / -78 °C

3: Et₃N; pyridine*SO₃; DMSO / CH₂Cl₂ / 0.33 h / 20 °C

4: 16.8 g / Et₃N / toluene / 12 h / 20 °C

5: 62 percent / chemical manganese dioxide; pyridine / benzene / 12 h / Heating

6: 91 percent / DIBAL / diethyl ether; hexane / 0.5 h / -78 °C

7: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

8: 344 mg / LiBr / acetone; CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; manganese(IV) oxide; sulfur trioxide pyridine complex; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium bromide; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene; 3: Parikh-Doering oxidation;

DOI:10.1016/S0040-4020(03)01020-2

upstream raw materials:

4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

3-((tert-butyl(diphenyl)silyl)oxy)-2,2-dimethylpropanoic acid

3-(tert-butyldiphenylsilyloxy)-2,2-dimethylpropanamide

3-(tert-butyldiphenylsilyloxy)-2,2-dimethylpropanethioamide

Downstream raw materials:

(2E)-4-{2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazol-4-yl}but-2-en-1-ol

2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-prop-2-ynylthiazole

2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-hex-5-en-2-ynylthiazole

(E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole