(Z)-2-bromo-3-(4-(dimethylamino)phenyl)acrylic acid methyl ester

Base Information

• Chemical Name: (Z)-2-bromo-3-(4-(dimethylamino)phenyl)acrylic acid methyl ester
• CAS No.: 55420-26-3
• Molecular Formula: C₁₂H₁₄BrNO₂
• Molecular Weight: 284.153
• Mol file: 55420-26-3.mol

Synonyms:(Z)-2-bromo-3-(4-(dimethylamino)phenyl)acrylic acid methyl ester

Chemical Property of (Z)-2-bromo-3-(4-(dimethylamino)phenyl)acrylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (Z)-2-bromo-3-(4-(dimethylamino)phenyl)acrylic acid methyl ester

There total 5 articles about (Z)-2-bromo-3-(4-(dimethylamino)phenyl)acrylic acid methyl ester 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: 98.0%

bromoacetic acid methyl ester (96-32-2) + 4-dimethylamino-benzaldehyde (100-10-7) → (Z)-2-bromo-3-(4-(dimethylamino)phenyl)acrylic acid methyl ester (55420-26-3)

Guidance literature:

bromoacetic acid methyl ester; 4-dimethylamino-benzaldehyde; With titanium tetrachloride; In dichloromethane; at 20 ℃; for 0.666667h; Inert atmosphere;

With triethylamine; In dichloromethane; at 20 - 30 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c3ob41592a

Reference yield:

4-dimethylamino-benzaldehyde (100-10-7) + methyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-2-bromoacetate (287481-44-1) → (Z)-2-bromo-3-(4-(dimethylamino)phenyl)acrylic acid methyl ester (55420-26-3) + (E)-2-bromo-3-(4-dimethylaminophenyl)acrylic acid methyl ester

Guidance literature:

methyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-2-bromoacetate; With 18-crown-6 ether; potassium tert-butylate; In tetrahydrofuran; acetonitrile; at -78 ℃; for 0.5h;

4-dimethylamino-benzaldehyde; In tetrahydrofuran; acetonitrile; at -78 ℃; for 0.3h;

DOI:10.1016/S0040-4020(00)00811-5

Reference yield:

methyl 3-(p-dimethylaminophenyl)-2-propenoate (63511-96-6,71348-26-0,7560-48-7) → (Z)-2-bromo-3-(4-(dimethylamino)phenyl)acrylic acid methyl ester (55420-26-3)

Guidance literature:

upstream raw materials:

methyl 3-(p-dimethylaminophenyl)-2-propenoate

4-dimethylamino-benzaldehyde

methyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-2-bromoacetate

bromoacetic acid methyl ester

Downstream raw materials:

trans-α-bromo-4-dimethylamino-cinnamic acid

1-(4-dimethylamino-phenyl)-ethanone-phenylhydrazone

4'-dimethylaminoacetophenone

methyl 5-(4-(dimethylamino)phenyl)-1H-1,2,3-triazole-4-carboxylate