Sodium Carbonate → 4'-[(4-Hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]-4-biphenyl carbonitrile

HRID 229296Notes

Reaction equation

HRID 229296 reaction equation
CS([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[C:25]3[CH2:30][C:29]([CH3:32])([CH3:31])[CH2:28][C:27]([CH3:34])([CH3:33])[CH2:26]3)[C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)=O.BrC1C=CC(C(=C2CC(C)(C)CC(C)(C)C2)C2C=CC(O)=CC=2)=CC=1.[C:60](C1C=CC(B(O)O)=CC=1)#[N:61].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>[OH:24][C:21]1[CH:22]=[CH:23][C:18]([C:17](=[C:25]2[CH2:30][C:29]([CH3:31])([CH3:32])[CH2:28][C:27]([CH3:34])([CH3:33])[CH2:26]2)[C:14]2[CH:15]=[CH:16][C:11]([C:8]3[CH:7]=[CH:6][C:5]([C:60]#[N:61])=[CH:10][CH:9]=3)=[CH:12][CH:13]=2)=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 111557414-[[4'-(Methylsulfonyl)-4-biphenylyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenolHCID 686543984-[(4-Bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

Product 1

HCID 117745144'-[(4-Hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]-4-biphenyl carbonitrileYield 74%

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)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol (14) (0.200 g, 0.5 mmol), PdCl2(PPh3)2 (0.035 g, 0.05 mmol), (4-cyanophenyl)boronic acid (0.165 g, 1.0 mmol), aqueous 2 M Na2CO3 (1.0 mL, 0.106 g, 1.0 mmol) solution, and 4:1 THF:H2O (5 mL) under a nitrogen atmosphere. The reaction mixture was refluxed for 12 h. Regular work-up and purification gave 0.155 g (74%) of the title compound (238) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.30 (s, 1H), 7.88 (d, J=8.4 Hz, 1H), 7.87 (d, J=4.8 Hz, 2H), 7.85 (d, J=8.4 Hz, 1H), 7.67 (d, J=8.0 Hz, 3H), 7.25 (d, J=8.4 Hz, 2H), 6.95 (d, J=8.8 Hz, 2H), 6.67 (d, J=8.4 Hz, 2H), 1.92 (br s, 4H), 1.25 (s, 2H), 0.88 (s, 12H). LCMS (APCI): m/z 419.97 (M−H)−.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 h
  2. customRegular work-up and purification

Sources & evidence

ORD record
ord-b2076e70f0464bf0b1cef9f7d95ed34c
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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