Methyl 4-fluorobenzoate → Methyl cis-4-fluorocyclohexanecarboxylate

HRID 414648

Reaction equation

HRID 414648 reaction equation
Cl[C:2]1([F:12])[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.ClC1CCC(C(OC)=O)CC1.COC(=O)C1C=CC(F)=CC=1>[Pd].ClC1C=CC=CC=1Cl>[F:12][CH:2]1[CH2:3][CH2:4][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 67878Methyl 4-fluorobenzoateHCID 143656621-Chloro-1-fluoro-4-carbomethoxy-cyclohexaneHCID 212815911-Chloro-4-carbomethoxy cyclohexane

Product 1

HCID 21281592Methyl cis-4-fluorocyclohexanecarboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
300 °C

Procedure

A mixture of 1.2 parts of 1-chloro-1-fluoro-4-carbomethoxy-cyclohexane and 4.8 parts of o-dichlorobenzene were added to a bed of 2% palladium on carbon maintained at 300° C. A stream of nitrogen at 400 cc/min. swept the products into two cold traps at 0° C. and -80° C. to yield 3.84 parts of combined products. Analysis by gas chromatography and mass spectrometry indicated complete reaction to yield 85% 1-fluoro-4-carbomethoxy-cyclohexane, 5% 1-chloro-4-carbomethoxy-cyclohexane and 10% methyl-4-fluorobenzoate, excluding the solvent.

Workup

  1. customat 0° C.
  2. custom-80° C. to yield 3.84 parts of combined products
  3. customreaction

Sources & evidence

ORD record
ord-0ce02448cff94ef2b6e7e893ec8ecb9d
Source dataset
uspto-grants-1988_12
Patent number
US04792618

Linked notes

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