# US 2014/0194654 A1 · Process for Producing Alpha-Fluoroaldehydes

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- Number: US 2014/0194654 A1
- Document ID: US20140194654A1
- Status: Published application
- Kind: A1
- Application number: 14/233,629
- Filed: 2012-07-24
- Published: 2014-07-10
- Earliest claimed: 2011-08-03
- Assignees: Central Glass Company, Limited
- Inventors: Akihiro Ishii; Takashi Ootsuka; Mari Imamura; Takayuki Nishimiya; Kazuto Kimura
- Web page: https://patentgrep.com/patent/US20140194654A1

## CPC

- C07C 45/41: by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
- B01J 31/189: {containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand}
- C07C 41/50: by reactions producing [IMAGE cpc-sch-C07C-0958.gif] groups
- B01J 2231/641: Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J 2531/821: Ruthenium
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

A production process of an α-fluoroaldehyde according to the present invention includes reaction of an α-fluoroester with hydrogen gas (H2) in the presence of a ruthenium complex. It is possible in the present invention to allow relatively easy industrial production of the α-fluoroaldehyde and to directly obtain, as stable synthetic equivalents of the α-fluoroaldehyde, not only a hydrate (as obtained by conventional techniques) but also a hemiacetal that is easy to purify and is of high value in synthetic applications. The present invention provides solutions to all problems in the conventional techniques and establishes the significantly useful process for production of the α-fluoroaldehyde.

## Claims

### Claim 1

A process for producing an α-fluoroaldehyde of the general formula [3], comprising: reaction of an α-fluoroester of the general formula [1] with hydrogen gas (H2) in the presence of a ruthenium complex of the general formula [2]
where R1 represents a halogen atom or a haloalkyl group; and R2 represents an alkyl group or a substituted alkyl group,
where R each independently represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aromatic ring group or a substituted aromatic ring group; Ar each independently represents an aromatic ring group or a substituted aromatic ring group; X each independently represents a ligand with a formal charge of −1 or 0 (with the proviso that the sum of the formal charges of three X is −2); and n each independently represents an integer of 1 or 2,
where R1 has the same meaning as in the general formula [1].

### Claim 2 (depends on 1)

The process according to claim 1, wherein the reaction is performed in the presence of a base.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the ruthenium complex of the general formula [2] is a ruthenium complex of the general formula [4]
where Ph represents a phenyl group.

### Claim 4 (depends on 1)

The process according to claim 1 any one of claim 1, wherein the α-fluoroester of the general formula [1] is an α-fluoroester of the general formula [5]; and the α-fluoroaldehyde of the general formula [3] is an α-fluoroaldehyde of the general formula [6]
where R3 is an alkyl group,

### Claim 5 (depends on 1)

The process according to claim 1, wherein the reaction is performed at a hydrogen pressure of 2 MPa or lower.

### Claim 6 (depends on 5)

The process according to claim 5, wherein the reaction is performed at a hydrogen pressure of 1 MPa or lower.

### Claim 7 (depends on 6)

The process according to claim 6, wherein the reaction is performed at a hydrogen pressure of 0.5 MPa or lower.

### Claim 8

A process for producing an α-fluoroaldehyde of the general formula [3], comprising: reaction of an α-fluoroester of the general formula [1] with hydrogen gas (H2) in the presence of a ruthenium catalyst
where R1 represents a halogen atom or a haloalkyl group; and R2 represents an alkyl group or a substituted alkyl group,
where R1 has the same meaning as in the general formula [1].

### Claim 9 (depends on 8)

The process according to claim 8, wherein the ruthenium catalyst is a homogeneous catalyst.