Potassium Carbonate → ({4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene) methyl]phenyl}oxy)acetonitrile

HRID 2241032Notes

Reaction equation

HRID 2241032 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:16]2[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]([CH3:25])([CH3:24])[CH2:17]2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]#[N:35]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[C:16]2[CH2:17][C:18]([CH3:25])([CH3:24])[CH2:19][C:20]([CH3:23])([CH3:22])[CH2:21]2)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:33][C:34]#[N:35])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 111635614-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

Product 1

HCID 11992564({4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene) methyl]phenyl}oxy)acetonitrileYield 72.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The o-alkylation procedure described for 10 (example 5, step 2) was employed. To a stirred suspension of 4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene) methyl]phenol 9 (0.508 g, 1.5 mmol), K2CO3 (0.414 g, 3.0 mmol), and acetone (50 mL) was added, under N2 at RT, bromoacetonitrile (0.21 mL, 3.0 mmol). The reaction mixture was refluxed for 4 h, cooled to RT, and filtered. Standard work-up followed by purification afforded 0.410 g (72%) of the title compound 14 as a white foam. mp 100-101° C. 1H NMR (300 MHz, CDCl3): δ 7.18-7.11 (m, 4H), 6.99 and 6.97 (dd, J1=8.7 Hz, J2=8.7 Hz, 2H), 6.92 (d, J=8.7 Hz, 2H), 4.76 (s, 2H), 1.98 (s, 2H), 1.97 (s, 2H), 1.32 (s, 2H), 0.96 (s, 12H). LCMS (ESI): m/z 376 (M−H)−. Anal. Calcd for C25H28FNO, C, 79.54, H, 7.48; N, 3.71. Found: C, 79.21, H, 7.46; N, 3.73.

Workup

  1. additionwas added, under N2 at RT
  2. temperatureThe reaction mixture was refluxed for 4 h
  3. filtrationfiltered
  4. customStandard work-up followed by purification

Sources & evidence

ORD record
ord-9920d1069ec54aa99e20ab377bceec31
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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