Sodium Carbonate → 4'-[Cyclooctylidene(4-hydroxyphenyl)methyl]-4-biphenylcarbonitrile

HRID 1716149Notes

Reaction equation

HRID 1716149 reaction equation
CS(C1C=CC(C2C=CC(C(=C3CC(C)(C)CC(C)(C)C3)C3C=CC(O)=CC=3)=CC=2)=CC=1)(=O)=O.Br[C:36]1[CH:41]=[CH:40][C:39]([C:42](=[C:50]2[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]2)[C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=2)=[CH:38][CH:37]=1.[C:58]([C:60]1[CH:65]=[CH:64][C:63](B(O)O)=[CH:62][CH:61]=1)#[N:59].C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C1COCC1>[C:50]1(=[C:42]([C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=2)[C:39]2[CH:38]=[CH:37][C:36]([C:63]3[CH:64]=[CH:65][C:60]([C:58]#[N:59])=[CH:61][CH:62]=3)=[CH:41][CH:40]=2)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 111557414-[[4'-(Methylsulfonyl)-4-biphenylyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenolHCID 686544754-[(4-Bromophenyl)(cyclooctylidene)methyl]phenol

Product 1

HCID 113383804'-[Cyclooctylidene(4-hydroxyphenyl)methyl]-4-biphenylcarbonitrileYield 76%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The Suzuki protocol described for (163) was employed. A round-bottomed flask was charged with 4-[(4-bromophenyl)(cyclooctylidene)methyl]phenol (49) (0.140 g, 0.37 mmol), PdCl2(PPh3)2 (0.027 g, 0.05 mmol), (4-cyanophenyl)boronic acid (0.109 g, 1.0 mmol), aqueous 2 M Na2CO3 (0.7 mL, 0.74 mL, 0.079 g, 1.0 mmol) solution, and 4:1 THF:H2O mixture (5 mL) under a nitrogen atmosphere. The reaction mixture was refluxed for 6 h. Upon regular work-up and purification gave 0.110 g (76%) of the title compound (239) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.32 (s, 1H), 7.86 (d, J=4.4 Hz, 1H), 7.85 (d, J=8.4 Hz, 2H), 7.84 (d, J=8.4 Hz, 1H), 7.67 (d, J=8.00 Hz, 2H), 7.24 (d, J=8.00 Hz, 2H), 6.95 (d, J=8.4 Hz, 2H), 6.68 (d, J=8.00 Hz, 2H), 2.21 (br s, 4H), 1.61 (br s, 2H), 1.49 (br m, 8H). LCMS (ESI): m/z 392.21 (M−H)−.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customUpon regular work-up and purification

Sources & evidence

ORD record
ord-4a618e937a484f1a9c6be3b892181b81
Source dataset
uspto-grants-2010_09
Patent number
US07799828B2

Reaction notes

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