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

HRID 325168
Notes
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Reaction equation

HRID 325168 reaction equation
[C:1]([CH:5]1CCC(=O)CC1)(C)([CH3:3])[CH3:2].C(N(S(F)(F)[F:18])CC)C.B(F)(F)F.CCOCC.[F:30][C:31]1[CH:36]=[CH:35][C:34](OC)=[CH:33][CH:32]=1>C(Cl)Cl>[F:30][C:31]1([F:18])[CH2:36][CH2:35][CH:34]([C:1]([CH3:5])([CH3:3])[CH3:2])[CH2:33][CH2:32]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 73924-tert-ButylcyclohexanoneHCID 8000Boron trifluoride etherateHCID 99874-FluoroanisoleHCID 123472(Diethylamino)sulfur trifluoride

Product 1

HCID 6404994-Tert-butyl-1,1-difluorocyclohexaneYield 67%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A solution of 4-t-butylcyclohexanone (308 mg, 2.0 mmol) in CH2Cl2 (10.0 mL) was added to diethylaminosulfur trifluoride (483 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 67% 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-e98883bcad9f48b1850604966c62e288
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06222064B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes