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Process for the preparation of aryl alcohols and heteroaryl alcohols

A kind of aryl and alkyl technology, applied in the field of preparation of aryl alcohol and heteroaryl alcohol, can solve the problems such as yield loss and complexity

Active Publication Date: 2022-01-18
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, these syntheses are often complex and / or performed in multiple reaction steps, which leads to loss of yield

Method used

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  • Process for the preparation of aryl alcohols and heteroaryl alcohols
  • Process for the preparation of aryl alcohols and heteroaryl alcohols
  • Process for the preparation of aryl alcohols and heteroaryl alcohols

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0098] Embodiment 1.1, the preparation of 2-oxaborolane and 1,2-oxaborolane

Embodiment 11

[0099] Example 1.1.2-butoxy-1,2-oxaborolane

[0100]

[0101] The title compound was prepared according to WO 2009 / 046098 A1 by hydroboration and transesterification with butanol.

Embodiment 12

[0102] Example 1.2.2-Ethoxy-1,2-oxaborolane

[0103]

[0104] The starting material 2-butoxy-1,2-oxaborolane (1 g) was stirred in 10 ml EtOH at 60° C. for 120 minutes and after 4-8 hours was subjected to vacuum at 100 mbar distilled. First, EtOH and BuOH are separated off, and then the product 2-ethoxy-1,2-oxaborolane is distilled off.

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Abstract

The present invention relates to a process for the preparation of aryl and heteroaryl alcohols by coupling aromatic halogen or pseudohalogen compounds to cyclic boronic esters.

Description

technical field [0001] The present invention relates to a process for the preparation of aryl and heteroaryl alcohols by coupling aromatic halogen or pseudohalogen compounds to cyclic boronic esters. Background technique [0002] Types of 1 Aryl and Heteroaryl Alcohols [0003] [0004] are known, inter alia, as pharmaceutically active compounds or precursors thereof, or also as performance chemicals, such as liquid crystals or precursors thereof. compound 2 and 3 Can be referenced by way of example. [0005] [0006] Efficient and feasible access to struct types 1 Necessary for economical preparation. So far, type 1 The synthesis of derivatives has mainly proceeded by reaction of precursor structures, usually in a reductive manner, as outlined in Scheme 1 by the example of C3 alcohols. [0007] [0008] Scheme 1. Ar = aryl, HetAr = heteroaryl, M = metal, PG = protecting group, R = alkyl. [0009] However, these syntheses are often complex and / or performed ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/14C07C39/11C07C33/46C07C33/26C07C33/20C07C33/24C07C29/36
CPCC07C29/36C07C33/20C07C33/24C07C33/26C07C33/46C07C39/11C07D311/14B01J23/44C07C29/32C07F7/1804C07C33/50C07C33/22C07C33/18
Inventor A·巴特M·赫尔姆雷驰
Owner MERCK PATENT GMBH
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