3(2R,3R),4(R) 3-<2-bromo-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone

Base Information

• Chemical Name: 3(2R,3R),4(R) 3-<2-bromo-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone
• CAS No.: 161970-64-5
• Molecular Formula: C₂₂H₂₄BrNO₄
• Molecular Weight: 446.341
• Mol file: 161970-64-5.mol

Synonyms:3(2R,3R),4(R) 3-<2-bromo-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone

Chemical Property of 3(2R,3R),4(R) 3-<2-bromo-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3(2R,3R),4(R) 3-<2-bromo-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone

There total 9 articles about 3(2R,3R),4(R) 3-<2-bromo-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone 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:

3,5-dimethylmethoxybenzene (874-63-5) → 3(2R,3R),4(R) 3-<2-bromo-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone (161970-64-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / Br₂ / CCl₄ / -25 °C

2: 1.) Mg / 1.) THF, reflux, 4 h, 2.) THF, 0 deg C to RT; RT, 1 h

3: potassium tert-butoxide / tetrahydrofuran / 2 h / Ambient temperature

4: LiOH*H₂O / methanol; H₂O

5: 1.) pivaloyl chloride, triethylamine / 1.) THF, -78 deg C, 15 min then 0 deg C, 45 min, 2.) THF, -78 deg C, 20 min then RT, 2 h

6: CuBr*(CH₃)2S / tetrahydrofuran; various solvent(s); diethyl ether / -4 deg C, 90 min; RT, overnight

7: 1.) diisopropylethylamine, di-n-butylborontriflate, 2.) N-bromosuccinimide / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 2 h; -78 to -4 deg C

With lithium hydroxide; N-Bromosuccinimide; copper(I) bromide dimethylsulfide complex; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; bromine; pivaloyl chloride; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; water;

DOI:10.1016/0040-4020(94)00996-8

Reference yield:

4-methoxy-2,6-dimethylbenzylaldehyde (19447-00-8) → 3(2R,3R),4(R) 3-<2-bromo-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone (161970-64-5)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium tert-butoxide / tetrahydrofuran / 2 h / Ambient temperature

2: LiOH*H₂O / methanol; H₂O

3: 1.) pivaloyl chloride, triethylamine / 1.) THF, -78 deg C, 15 min then 0 deg C, 45 min, 2.) THF, -78 deg C, 20 min then RT, 2 h

4: CuBr*(CH₃)2S / tetrahydrofuran; various solvent(s); diethyl ether / -4 deg C, 90 min; RT, overnight

5: 1.) diisopropylethylamine, di-n-butylborontriflate, 2.) N-bromosuccinimide / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 2 h; -78 to -4 deg C

With lithium hydroxide; N-Bromosuccinimide; copper(I) bromide dimethylsulfide complex; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; pivaloyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; water;

DOI:10.1016/0040-4020(94)00996-8

Reference yield:

2-bromo-5-methoxy-1,3-dimethyl-benzene (6267-34-1) → 3(2R,3R),4(R) 3-<2-bromo-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone (161970-64-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Mg / 1.) THF, reflux, 4 h, 2.) THF, 0 deg C to RT; RT, 1 h

2: potassium tert-butoxide / tetrahydrofuran / 2 h / Ambient temperature

3: LiOH*H₂O / methanol; H₂O

4: 1.) pivaloyl chloride, triethylamine / 1.) THF, -78 deg C, 15 min then 0 deg C, 45 min, 2.) THF, -78 deg C, 20 min then RT, 2 h

5: CuBr*(CH₃)2S / tetrahydrofuran; various solvent(s); diethyl ether / -4 deg C, 90 min; RT, overnight

6: 1.) diisopropylethylamine, di-n-butylborontriflate, 2.) N-bromosuccinimide / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 2 h; -78 to -4 deg C

With lithium hydroxide; N-Bromosuccinimide; copper(I) bromide dimethylsulfide complex; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; pivaloyl chloride; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; water;

DOI:10.1016/0040-4020(94)00996-8

upstream raw materials:

3(3S),4(R) 3-<3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone

3,5-dimethylmethoxybenzene

2-bromo-5-methoxy-1,3-dimethyl-benzene

4-methoxy-2,6-dimethylbenzylaldehyde

Downstream raw materials:

3(2S,3R),4(R) 3-<2-azido-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone

(2S,3R) 2-azido-3-(4'-methoxy-2',6'-dimethylphenyl)butanoic acid

(2S,3R) 2-amino-3-(2',6'-dimethyl-4'-hydroxyphenyl)butanoic acid