4-tert-Butylcyclohexanone → 4-tert-butyl-1,1-difluorocyclohexane

HRID 325169Notes

Reaction equation

HRID 325169 reaction equation
[C:1]([CH:5]1CCC(=O)CC1)(C)([CH3:3])[CH3:2].C(N(S(F)(F)[F:22])C1C=CC=CC=1)C.B(F)(F)F.CCOCC.[F:34][C:35]1[CH:40]=[CH:39][C:38](OC)=[CH:37][CH:36]=1>C(Cl)Cl>[F:34][C:35]1([F:22])[CH2:40][CH2:39][CH:38]([C:1]([CH3:5])([CH3:3])[CH3:2])[CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 73924-tert-ButylcyclohexanoneHCID 8000Boron trifluoride etherateHCID 99874-FluoroanisoleHCID 20650010Sulfur, (N-ethylbenzenaminato)trifluoro-, (T-4)-

Product 1

HCID 6404994-tert-butyl-1,1-difluorocyclohexaneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-t-butylcyclohexanone (308 mg, 2.0 mmol) in CH2Cl2 (10.0 mL) was added to N-ethyl-N-phenylaminosulfur trifluoride (627 mg, 3.0 mmol ) at room temperature under N2. BF3.OEt2 (100 mL) was added and the mixture was stirred for 6 h at room temperature. The mixture was washed with saturated NaHCO3, dried (Na2SO4), filtered and evaporated in vacuo. Proton and Fluorine NMR with 4-fluoroanisole (2 mmol) as internal standard showed that a 99% yield of 1,1-difluoro-4-t-butylcyclohexane was obtained.

Workup

  1. washThe mixture was washed with saturated NaHCO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-edf018d1ba4442aaa2d395a1591c8bd7
Source dataset
uspto-grants-2001_04
Patent number
US06222064B1

Reaction notes

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