4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate

Base Information

• Chemical Name: 4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate
• CAS No.: 145103-58-8
• Molecular Formula: C₁₃H₁₄BrNO₇S
• Molecular Weight: 408.227

Synonyms:4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate

Chemical Property of 4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate

Chemical Property:

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Technology Process of 4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate

There total 2 articles about 4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate 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: 88.0%

methanesulfonyl chloride (124-63-0) + (4R,5R)-4-(4-Bromo-phenyl)-5-hydroxymethyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid methyl ester (145103-57-7) → 4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate (145103-58-8)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1248/cpb.40.1921

Reference yield:

3,5-bis(methoxycarbonyl)-4-p-bromophenyl-2-isoxazoline-2-oxide (90018-65-8,90905-67-2,97053-69-5,145103-56-6) → 4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate (145103-58-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / NaBH₄ / tetrabenzylammonium chloride / H₂O; CH₂Cl₂ / 4 h / Ambient temperature

2: 88 percent / pyridine / Ambient temperature

With pyridine; sodium tetrahydroborate; Bn₄NCl; In dichloromethane; water;

DOI:10.1248/cpb.40.1921

Reference yield: 76.0%

4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate (145103-58-8) → 4-(4-bromo-2-chlorophenyl)-5-hydroxy-3-methoxycarbonyl-5,6-dihydro-4H-1,2-oxazine

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 40 ℃;

DOI:10.3987/COM-93-6469

upstream raw materials:

methanesulfonyl chloride

(4R,5R)-4-(4-Bromo-phenyl)-5-hydroxymethyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid methyl ester

3,5-bis(methoxycarbonyl)-4-p-bromophenyl-2-isoxazoline-2-oxide

Downstream raw materials:

4-p-bromophenyl-5-hydroxy-3-methoxycarbonyl-5,6-dihydro-4H-1,2-oxazine

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