1,3,5-Trichloro-2,4,6-trifluorobenzene → 1-(3,5-Dichloro-2,4,6-trifluorophenyl)perfluorocyclohexanol

HRID 428350Notes

Reaction equation

Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[C:5]([F:10])=[C:4]([Cl:11])[C:3]=1[F:12].C([Li])CCC.[F:18][C:19]1([F:34])[C:24]([F:26])([F:25])[C:23]([F:28])([F:27])[C:22]([F:30])([F:29])[C:21]([F:32])([F:31])[C:20]1=[O:33]>C(OCC)C>[Cl:11][C:4]1[C:3]([F:12])=[C:2]([C:20]2([OH:33])[C:21]([F:32])([F:31])[C:22]([F:30])([F:29])[C:23]([F:27])([F:28])[C:24]([F:25])([F:26])[C:19]2([F:18])[F:34])[C:7]([F:8])=[C:6]([Cl:9])[C:5]=1[F:10]

Participants

Conditions

Temperature: -78 °C

Procedure

Under a N2 atmosphere 29.5 g of 1,3,5-trichloro-2,4,6-trifluorobenzene (Oakwood Products, Inc.) were dissolved in 150 mL dry ethyl ether. The solution was cooled to −78° C. in an acetone/dry-ice bath, then treated with 62.7 mL n-butyllithium (2 M solution in hexanes) over a two-hour period. Stirring was continued for 3 hours at −78° C. Via syringe, 34.8 g perfluorocyclohexanone were added, and the mixture was stirred at room temperature for 16 hours. The reaction was quenched with dilute HCl and extracted with ethyl ether, and the extracts were dried (using MgSO4) and rotary evaporated. Vacuum distillation (118-120° C., 80-110 Pa) gave 37.3 g 1-(3,5-dichloro-2,4,6-trifluorophenyl)perfluorocyclohexanol (62% yield) as a colorless liquid.

Workup

stirringthe mixture was stirred at room temperature for 16 hours
customThe reaction was quenched with dilute HCl
extractionextracted with ethyl ether
dry with materialthe extracts were dried (using MgSO4) and rotary evaporated
distillationVacuum distillation (118-120° C., 80-110 Pa)

Sources & evidence

ORD record: ord-9084b01b35594c5589fd91335e45b800
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313245B1

Reaction notes

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