# US 7,612,240 B2 · Halophospholanes and their preparation

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- Number: US 7,612,240 B2
- Document ID: US7612240B2
- Status: Granted
- Kind: B2
- Application number: 12/091,410
- Filed: 2006-10-04
- Published: 2008-11-20
- Granted: 2009-11-03
- Earliest claimed: 2005-11-04
- Assignees: Evonik Degussa GmbH
- Inventors: Armin Börner; Jens Holz; Juan Almena; Renat Kadyrov; Axel Monsees; Thomas Riermeier
- Web page: https://patentgrep.com/patent/US7612240B2

## CPC

- C07F 9/65683: {the ring phosphorus atom being part of a phosphine}
- B01J 31/2433: {comprising aliphatic or saturated rings}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

The present invention is directed to a process for preparing compounds of the general formula (I). Compounds of the general formula (I) are advantageous precursors for preparing phospholane catalysts, especially bisphospholane catalysts. The invention therefore likewise provides for the use of the substances in question for preparing these catalysts.

## Claims

### Claim 1

Process for preparing compounds of the formula (I)
in which
* is a stereogenic center,
X is Cl, Br, or I,
R1 and R4 are each independently (C1-C8)-alkyl, (C1-C8)-alkoxy, HO—(C1-C8)-alkyl, (C2-C8)-alkoxyalkyl,(C6-C18)-aryl, (C7-C19)-aralkyl, (C3-C18)-heteroaryl, (C4-C19)-heteroaralkyl, (C1-C8)-alkyl-(C6-C18)-aryl, (C1-C8)-alkyl-(C3-C18)-heteroaryl, (C3-C8)-cycloalkyl, (C1-C8)-alkyl-(C3-C8)-cycloalkyl, or (C3-C8)-cycloalkyl-(C1-C8)-alkyl,
R2, R3 are each independently R1, OH or H, or
(a)
R1 and R2 form a (C3-C5)-alkylene bridge together,
(b) R2 and R3 form a (C3-C5)-alkylene bridge together,
(c) R1 and R3 form a (C3-C5)-alkylene bridge together, or
(d) R2 and R4 form a (C3-C5)-alkylene bridge together,
wherein
compounds of the formula (II)
in which
*, R1, R2, R3, R4 are each as defined above,
R, R′, R″ may each independently be R1,
are reacted with halogenated compounds selected from the group consisting of halocarbon compounds which lack double bonds in which the ratio of carbon atoms to halogen atoms is 1:≧2.5, CCl3CN, CCl3COOEt, CCl(3-x)HxC(═O)Cl, C2Cl4Br2, Cl2, Br2, I2.

### Claim 2 (depends on 1)

Process according to claim 1, wherein halogenated compounds selected from the group consisting of CCl4, CHCl3, C2Cl6, C2HCl5, C2Cl4Br2, Cl2, Br2, I2 are used.

### Claim 3 (depends on 1)

Process according to claim 1, wherein the reaction is carried out in an organic solvent selected from the group consisting of CH2Cl2 and CHCl3.

### Claim 4 (depends on 1)

Process according to claim 1, wherein the reaction is carried out at a temperature of 0-120° C.

### Claim 5

Compounds of the formula (I)
in which
* is a stereogenic center,
X is Cl, Br, or I,
R1 and R4 are each independently (C1-C8)-alkyl, (C1-C8)-alkoxy, HO—(C1-C8)-alkyl, (C2-C8)-alkoxyalkyl, (C6-C18)-aryl, (C7-C19)-aralkyl, (C3-C18)-heteroaryl, (C4-C19)-heteroaralkyl, (C1-C8)-alkyl-(C6-C18)-aryl, (C1-C8)-alkyl-(C3-C18)-heteroaryl, (C3-C8)-cycloalkyl, (C1-C8)-alkyl-(C3-C8)-cycloalkyl, or (C3-C8)-cycloalkyl-(C1-C8)-alkyl,
R2 and R3 are each independently R1, OH or H, or
(a) R1 and R2 form a (C3-C5)-alkylene bridge together,
(b) R2 and R3 form a (C3-C5)-alkylene bridge together,
(c) R1 and R3 form a (C3-C5)-alkylene bridge together, or
(d) R2 and R4 form a (C3-C5)-alkylene bridge together.

### Claim 6 (depends on 1)

Process according to claim 1 wherein the reaction is carried out at a temperature of 20-80° C.

### Claim 7 (depends on 1)

Process according to claim 1 wherein the reaction is carried out at a temperature of 30-50° C.