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
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.
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