(+)-methyl 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylate

Base Information

• Chemical Name: (+)-methyl 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylate
• CAS No.: 185851-38-1
• Molecular Formula: C₁₁H₁₅BrO₃
• Molecular Weight: 275.142
• Mol file: 185851-38-1.mol

Synonyms:(+)-methyl 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylate

Chemical Property of (+)-methyl 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-methyl 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylate

There total 10 articles about (+)-methyl 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylate 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: 96.0%

3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylic acid (185851-37-0) + methyl iodide (74-88-4) → (+)-methyl 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylate (185851-38-1)

Guidance literature:

With potassium carbonate; In acetone; for 4h; Ambient temperature;

DOI:10.1016/S0040-4020(99)00305-1

Reference yield:

3-bromo-2,4-dimethylpenta-1,3-diene (4773-87-9) → (+)-methyl 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylate (185851-38-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / 48 h / Heating

2: 32 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 0 deg C to room temp., 1 h

3: 45 percent / Na, 2-propanol / tetrahydrofuran / 168 h / 80 °C

4: 76 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 18 h / -15 °C

5: 1.) N₂O₄, AcONa, 2.) PhSH, CF₃COOH / 1.) 1,2-dichloroethane, CCl₄, 0 deg C, 16 h, 2.) CCl₄, 1,2-dichloroethane, room temp., 18 h

6: 96 percent / K₂CO₃ / acetone / 4 h / Ambient temperature

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; sodium acetate; sodium; dinitrogen tetraoxide; potassium carbonate; thiophenol; triethylamine; isopropyl alcohol; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1016/S0040-4020(99)00305-1

Reference yield:

3-bromo-2,2,4-trimethylcyclohex-3-ene carbonyl chloride (185851-20-1) → (+)-methyl 3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylate (185851-38-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 32 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 0 deg C to room temp., 1 h

2: 45 percent / Na, 2-propanol / tetrahydrofuran / 168 h / 80 °C

3: 76 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 18 h / -15 °C

4: 1.) N₂O₄, AcONa, 2.) PhSH, CF₃COOH / 1.) 1,2-dichloroethane, CCl₄, 0 deg C, 16 h, 2.) CCl₄, 1,2-dichloroethane, room temp., 18 h

5: 96 percent / K₂CO₃ / acetone / 4 h / Ambient temperature

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; sodium acetate; sodium; dinitrogen tetraoxide; potassium carbonate; thiophenol; triethylamine; isopropyl alcohol; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1016/S0040-4020(99)00305-1

upstream raw materials:

3-bromo-2,2,4-trimethylcyclohex-3-ene-5-one carboxylic acid

methyl iodide

3-bromo-2,4-dimethylpenta-1,3-diene

3-bromo-2,2,4-trimethylcyclohex-3-ene carbonyl chloride

Downstream raw materials:

(+)-methyl 3-bromo-5α-hydroxy-2,2,4-trimethylcyclohex-3-ene carboxylate